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‘Secondary’ Investing in Litigation Finance (part 2): Why, why now, and how to approach investing in Lit Fin Secondaries

‘Secondary’ Investing in Litigation Finance (part 2): Why, why now, and how to approach investing in Lit Fin Secondaries

The following article is part of an ongoing column titled ‘Investor Insights.’  Brought to you by Ed Truant, founder and content manager of Slingshot Capital, ‘Investor Insights’ will provide thoughtful and engaging perspectives on all aspects of investing in litigation finance.  Executive Summary
  • Evolution of Litigation Finance necessitates the need for a secondary market
  • Investing in Litigation Finance secondaries is much more difficult than other forms of private equity due to the inherent difficulty in valuing the ‘tail’
  • Experts should be utilized to assess case merits and valuation
  • Life cycle of litigation finance suggests timing is right for secondaries
Slingshot Insights:
  • Investing in the ‘tail’ of a portfolio, where most secondary transactions will take place, can be more difficult than primary investing
  • Dynamics of the ‘tail’ of a portfolio are inherently riskier than a whole portfolio, which is partially offset by enhanced information related to the underlying cases
  • Secondary portfolios are best reviewed by experts in the field and each significant investment should be reviewed extensively
  • Derive little comfort from portfolios that have been marked-to-market by the underlying manager
  • Investing in secondaries requires a discount to market value to offset the implied volatility associated with the tail
In part 1 of this article, I explored some of the basic concepts of secondary investing, specifically in the context of the commercial litigation finance asset class.  This article continues the discussion and explores some of the unique aspects and characteristic of the ‘tail’ of a litigation finance portfolio, why now is a particularly good time for secondary transactions and other investment considerations with respect to secondary investing. Investing in the ‘tail’ In a prior article, I made reference to three phases of risk in the context of litigation (there are more but let’s keep it simple for now).  As a case evolves, it moves from a phase where the case is “De-Risking” because more information is flowing to the point where both parties have an abundance of, and equal information about, the litigation (yet still have different perspectives based on subjective value judgments), which moves the case into something I referred to as the zone of “Optimal Resolution” (credit to John Rossos at Bridgepoint Financial who developed this ‘three phases of risk’ analogy). Optimal Resolution is a period of time where both parties understand what information the other party has, the legal precedents being referenced, and perhaps some insights into how similar cases would have been judged in the past.  With an abundance of information, the two parties should come together to form a conclusion around a reasonable settlement and bring the case to an end.  However, if they fail to do so, the case starts to enter into the “Re-Risk” stage where the parties typically commence with a trial or arbitration, at which stage both sides may get more entrenched in their positions and if they do the outcome ultimately becomes binary, as it will be decided by a third party (i.e., judge, arbitrator or a jury) without a vested economic interest in the outcome.  Any good litigator will tell you to avoid a binary outcome if at all possible, as these outcomes are quite unpredictable (i.e. your odds of winning may be better in Vegas). I make reference to these three phases because the ‘tail’ tends to capture the Re-Risk stage of litigation/arbitration, which is the riskiest part of the litigation process.  So, when investors are looking at a secondary portfolio of single case investments, they are almost by definition investing at the riskiest part of the lifecycle of the case.  Of course, that is not always the case, and it depends whether you are the plaintiff or the defendant.  If you are a plaintiff, you may have a number of interim procedural wins and so you may believe there is a stronger possibility of success as compared to when the manager first under-wrote the case.  Therefore, you may be feeling relatively good about your prospects. However, while one would think justice is equitable, consistent and repeatable, that is rarely the case, which makes this stage of the litigation process the most dangerous, as the plaintiff may be lulled into a false sense of security based on some procedural wins and damning evidence against the defendant. The fact that these cases are in the tail of the portfolio firmly suggests that (i) they have been going on for a long time, which means that (ii) you may have two entrenched, deep pocketed parties who are not likely to give in soon, which means that (iii) the outcome will more likely than not end up in a binary decision.  Of course, it may also mean that it is closer to resolution, as many cases have been settled on the ‘court room steps’. Accordingly, the risks are different than those of investing into a ‘blind pool’ portfolio where the cases have yet to be picked. In a nutshell, the investor in a secondary does not get the benefit of the early wins and relatively more attractive IRRs to offset the more binary characteristics of the tail, which likely includes bigger losses (if for no other reason than a loss in the tail means the original capital commitment has likely been fully consumed).  Since the secondary investor has to make his or her returns from the more binary portion of the portfolio, which means higher volatility as the probability of a loss is higher in the tail segment of the distribution (a well-known statistical characteristic), ultimately, it would be dangerous for a new investor to pay a premium, and conversely, it is likelier the investor will need to buy at a discount. But discount to what – original cost or current fair market value?  Discounting to cost is a fairly easy exercise, but may not be meaningful.  Discounting to fair market value is pretty challenging in the context of a tail comprised of single case investments, each of which is more likely than not in the Re-Risking stage of the investment life cycle.  Nevertheless, it is only logical that a secondary investor should treat the investment as though it was a new portfolio and underwrite every significant investment in the portfolio from scratch, to do otherwise would be reckless.  A “diligence light” approach is not acceptable given the potentially higher risks inherent in the tail and so as much, if not more, time should be spent underwriting secondary portfolios as compared to primary portfolios. Also recognize that when selling secondary portfolios the seller and their advisors are in ‘sell mode’, and so a second set of sober and skeptical eyes is probably the best way to value these assets.  An astute investor can also structure the investment by limiting its downside by negotiating a lower entry price in exchange for a sharing of the upside with the exiting investor, so that it becomes a ‘win-win’ transaction with the secondary investor getting some downside protection, and the exiting investor retaining some upside. A positive aspect of investing in the tail is that the majority of the legal spend has taken place and so your deployment risk is probably low, which essentially means that if you win, your ROI will likely be a multiple of a higher known number as compared to when the investment was originally underwritten. That’s IF you win!  It also means that you have the ability to determine the impact of fees on expected returns based on when the fees were charged in relation to when the cash was invested, which may help with the gross-to-net return spread issue that can be significant in litigation finance.  There is also the potential that these cases may settle relatively early in the life cycle of the secondary investor’s ownership period, which will likely generate stronger IRRs and MOICs, and hopefully minimize the ‘fee drag’ (the impact fees have on net investor returns). Why now? There has been much recent chatter in the litigation finance sector about secondary opportunities, so why now? Well, it’s mainly reflective of the extent of time the industry has been in existence.  The commercial litigation finance industry started in earnest between five and ten years ago in the US.  Accordingly, a meaningful amount of capital has been raised and a sufficient amount of time has passed to allow for the conditions necessary for secondaries – namely supply.  The supply mainly stems from a confluence of investor interest in liquidity for their longer dated investments, and GP interest in ‘putting some points on the board’, meaning they need to show some track record so they can raise a subsequent fund. Simply, the timing seems right, and when an institution needs a way to achieve liquidity for its portfolio, it will find a way to do so. How best to approach investing in secondary transactions? Different from other forms of private equity, acquiring litigation finance investments in the secondary market requires the expertise of a litigation finance fund manager.  I say this because of the risks inherent in the tail end of the portfolio, and the expertise required to assess this tail is the same expertise required to underwrite new investments.  It would be a mistake to confuse investing in secondary transactions in litigation finance with other private equity sectors like leveraged buy-out or venture capital, where the valuation metrics and approach to valuation are much more transparent and well accepted. Valuation in litigation finance is much more in the realm of ‘beauty is in the eye of the beholder’ (aka “a subjective value judgment”), with one group seeing much more value in a case than another based on their biases and experiences.  Managers that invest in secondaries should be prepared to do extensive diligence on a large part of the portfolio, and certainly those investments in the portfolio that appear riskier and disproportionately large relative to the average case size in the portfolio. The other important element is to ensure that you have a diversified portfolio.  If you are purchasing a tail portfolio, then it likely means there are fewer investments than what was present in the original portfolio earlier in its investment cycle; hence, there will be a higher degree of volatility, in statistical terms.  Since there are now fewer investments in the tail portfolio and the early resolutions likely provided strong returns, the remainder of the tail has to stand on its own merit and so it will be important to ensure the tail portfolio is large enough to be diversified in its own right.  To the extent it is not well diversified, I would consider spreading your overall secondary allocations across more than one portfolio, until you get a desired (target) degree of diversification (case types, case sizes, geographies, defendants, law firms, etc.) with a limited concentration risk within the portfolio.  A portfolio with 50 cases might seem diversified, but if three of those cases represent 30% of the capital and they all turn out to be losers (which is statistically a very real potential outcome), then it puts a lot of pressure on the remaining portfolio to both offset the large losses while simultaneously producing target returns for the portfolio as a whole. Lastly, I would consider putting in place an insurance wrapper for ‘first loss’ insurance.  This type of insurance can be expensive, and so you need to be prudent and careful not to over-insure.  You have to look at the risk of loss probabilistically, and such an analysis could show that you don’t likely have to insure 100% of the principal, but probably just a fraction of the principal, and preferably through first-loss coverage, where the insurer takes the obligation for the loss on the first, say, 20% – 30% of the portfolio (the riskiest portion, statistically speaking), and the investor is exposed for the remaining 70% – 80% (the decreasingly less risky portion). I think most secondary portfolios should be valued at a significant discount to market value with a range of probability-sequenced outcomes to triangulate to a valuation. The valuator should not lose sight of the fact that approximately 30% of litigation finance backed cases lose, and so this should be a starting point for the analysis of the potential value of the portfolio, and stress-tested from there to reflect the higher risk inherent in the ‘tail’.  However, there can also be specific investment opportunities which through the process of de-risking may represent better opportunities than they did before the de-risking process and the investor may be able to justify or may be forced to accept a higher valuation in order to be able to transact. In situations where the litigation is so significant that it can actually have an impact on a defendant’s publicly traded securities, you could also use options on the publicly traded securities of your counter-party to hedge your investment such that if you lose the case you make money on the hedge, and if you win the case, the cost of unravelling the hedge becomes the cost of an otherwise successful transaction.  Of course, any hedge will be imperfect as the stock price of the defendant can be influenced by a number of factors in addition to the outcome of the litigation, the very outcome you are trying to hedge. David Ross, Managing Director & Head of Private Credit at Northleaf Capital Partners notes: “We approach secondary transactions in a prudent and judicious manner with thorough analysis on concentration risk, deep dive on case merits and outcomes, as well as comprehensive financial diligence and modeling. We tend to mitigate investment risk by way of conservative structuring and cautious underlying assumptions that provide significant cushion for the investment.” It is only through a cautious approach that one can successfully invest in commercial litigation finance secondaries.  Other areas of litigation finance (consumer, law firm lending, etc.) will likely have different risks and portfolio characteristics that allow for less extensive diligence on the portfolio, which may be a consideration for some investors. Slingshot Insights For those investors interested in the litigation finance secondary market, I think it is important to approach the investment with caution and a high level of expert diligence to offset the implied volatility that the ‘tail’ of the portfolio offers.  It is also important to understand the motivations of the seller – a manager looking to create a track record will have different motivations than an investor who needs liquidity.  The seller’s motivations may also offer insight into the extent price can be negotiated. It is important not to lose sight of the typical loss rate of the industry and the fact that the tail should exhibit enhanced volatility (more losses) as compared to a whole portfolio, and so an investor should model their returns, and hence their entry price, accordingly. Should you choose to make a secondary investment, consider a variety of options to de-risk the investment by sharing risks and rewards with others (i.e. insurance providers or the vendor of the asset). Above all else, make sure your secondaries are diversified or part of a larger diversified pool of assets. As always, I welcome your comments and counter-points to those raised in this article.  Edward Truant is the founder of Slingshot Capital Inc. and an investor in the consumer and commercial litigation finance industry.  Slingshot Capital inc. is involved in the origination and design of unique opportunities in legal finance markets, globally, investing with and alongside institutional investors.
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A Framework for Measuring Tech ROI in Litigation Finance

This article was contributed by Ankita Mehta, Founder, Lexity.ai - a platform that helps litigation funds automate deal execution and prove ROI.

How do litigation funders truly quantify the return on investment from adopting new technologies? It’s the defining question for any CEO, CTO or internal champion. The potential is compelling: for context, according to litigation funders using Lexity’s AI-powered workflows, ROI figures of up to 285% have been reported.

The challenge is that the cost of doing nothing is invisible. Manual processes, analyst burnout, and missed deals rarely appear on a balance sheet — but they quietly erode yield every quarter.

You can’t manage what you can’t measure. This article introduces a pragmatic framework for quantifying the true value of adopting technology solutions, replacing ‘low-value’ manual tasks and processes with AI and freeing up human capital to focus on ‘high-value’ activities that drive bottom line results  .

A Pragmatic Framework for Measuring AI ROI

A proper ROI calculation goes beyond simple time savings. It captures two distinct categories:

  1. Direct Cost Savings – what you save
  2. Increased Value Generation – what you gain

The ‘Cost’ Side (What You Save)

This is the most straightforward calculation, focused on eliminating “grunt work” and mitigating errors.

Metric 1: Direct Time Savings — Eliminating Manual Bottlenecks 

Start by auditing a single, high-cost bottleneck. For many funds, this is the Preliminary Case Assessment, a process that often takes two to three days of an expert analyst's time.

The calculation here is straightforward. By multiplying the hours saved per case by the analyst's blended cost and the number of cases reviewed, a fund can reveal a significant hard-dollar saving each month.

Consider a fund reviewing 20 cases per month. If a 2-day manual assessment can be cut to 4 hours using an AI-powered workflow, the fund reallocates hundreds of analyst-hours every month. That time is now moved from low-value data entry to high-value judgment and risk analysis.

Metric 2: Cost of Inconsistent Risk — Reducing Subjectivity 

This metric is more complex but just as critical. How much time is spent fixing inconsistent or error-prone reviews? More importantly, what is the financial impact of a bad deal slipping through screening, or a good deal being rejected because of a rushed, subjective review?

Lexity’s workflows standardise evaluation criteria and accelerate document/data extraction, converting subjective evaluations into consistent, auditable outputs. This reduces rework costs and helps mitigate hidden costs of human error in portfolio selection.

The ‘Benefit’ Side (What You Gain)

This is where the true strategic upside lies. It’s not just about saving time—it’s about reinvesting that time into higher-value activities that grow the fund.

Metric 3: Increased Deal Capacity — Scaling Without Headcount Growth

What if your team could analyze more deals with the same staff? Time saved from automation becomes time reallocated to new higher value opportunities, dramatically increasing the value of human contributions.

One of the funds working with Lexity have reported a 2x to 3x increase in deal review capacity without a corresponding increase in overhead. 

Metric 4: Cost of Capital Drag — Reducing Duration Risk 

Every month a case extends beyond its expected closing, that capital is locked up. It is "dead" capital that could have been redeployed into new, IRR-generating opportunities.

By reducing evaluation bottlenecks and creating more accurate baseline timelines from inception, a disciplined workflow accelerates the entire pipeline. 

This figure can be quantified by considering the amount of capital locked up, the fund's cost of capital, and the length of the delay. This conceptual model turns a vague risk ("duration risk") into a hard number that a fund can actively manage and reduce.

An ROI Model Is Useless Without Adoption

Even the most elegant ROI model is meaningless if the team won't use the solution. This is how expensive technology becomes "shelf-ware."

Successful adoption is not about the technology; it's about the process. It starts by:

  1. Establish Clear Goals and Identify Key Stakeholders: Set measurable goals and a baseline. Identify stakeholders, especially the teams performing the manual tasks- they will be the first to validate efficiency gains.
  2. Targeting "Grunt Work," Not "Judgment": Ask “What repetitive task steals time from real analysis?” The goal is to augment your experts, not replace them.
  3. Starting with One Problem: Don't try to "implement AI." Solve one high-value bottleneck, like Preliminary Case Assessment. Prove the value, then expand. 
  4. Focusing on Process Fit: The right technology enhances your workflow; it doesn’t complicate it.

Conclusion: From Calculation to Confidence

A high ROI isn't a vague projection; it’s what happens when a disciplined process meets intelligent automation.

By starting to measure what truly matters—reallocated hours, deal capacity, and capital drag—fund managers can turn ROI from a spreadsheet abstraction into a tangible, strategic advantage.

By Ankita Mehta Founder, Lexity.ai — a platform that helps litigation funds automate deal execution and prove ROI.

Burford Capital’s $35 M Antitrust Funding Claim Deemed Unsecured

By John Freund |

In a recent ruling, Burford Capital suffered a significant setback when a U.S. bankruptcy court determined that its funding agreement was not secured status.

According to an article from JD Journal, Burford had backed antitrust claims brought by Harvest Sherwood, a food distributor that filed for bankruptcy in May 2025, via a 2022 financing agreement. The capital advance was tied to potential claims worth about US$1.1 billion in damages against meat‑industry defendants.

What mattered most for Burford’s recovery strategy was its effort to treat the agreement as a loan with first‑priority rights. The court, however, ruled the deal lacked essential elements required to create a lien, trust or other secured interest. Instead, the funding was classified as an unsecured claim, meaning Burford now joins the queue of general creditors rather than enjoying priority over secured lenders.

The decision carries major consequences. Unsecured claims typically face a much lower likelihood of full recovery, especially in estates loaded with secured debt. Here, key assets of the bankrupt estate consist of the antitrust actions themselves, and secured creditors such as JPM Chase continue to dominate the repayment waterfall. The ruling also casts a spotlight on how litigation‑funding agreements should be structured and negotiated when bankruptcy risk is present. Funders who assumed they could elevate their status via contractual design may now face greater caution and risk.

Manolete Partners PLC Posts Flat H1 as UK Insolvency Funding Opportunity Grows

By John Freund |

The UK‑listed litigation funder Manolete Partners PLC has released its interim financial results for the half‑year ended 30 September 2025, revealing a stable but subdued performance amid an expanding insolvency funding opportunity.

According to the company announcement, total revenue fell to £12.7 million (down 12 % from £14.4 million a year earlier), while realised revenue slipped to £14.0 million (down 7 % from £15.0 million). Operating profit dropped sharply to £0.1 million, compared to £0.7 million in the prior period—though excluding fair value write‑downs tied to the company’s truck‑cartel portfolio, underlying profit stood at £2.0 million.

The business completed 146 cases during the period (up 7 % year‑on‑year) and signed 146 new case investments (up nearly 16 %). Live cases rose to 446 from 413 a year earlier, and the total estimated settlement value of new cases signed in the period was claimed to be 31 % ahead of the prior year. Cash receipts were flat at about £14.5 million, while net debt improved to £10.8 million (down from £11.9 million). The company’s cash balance nearly doubled to £1.1 million.

In its commentary, Manolete emphasises the buoyant UK insolvency backdrop — particularly the rise of Creditors’ Voluntary Liquidations and HMRC‑driven petitions — as a tailwind for growth. However, the board notes the first half was impacted by a lower‑than‑average settlement value and a “quiet summer”, though trading picked up in September and October. The firm remains confident of stronger average settlement values and a weighting of realised revenues toward the second half of the year.