Episode Summary: How I Invest with David Weisburd Episode 252: Inside the Mind of a 29-Year-Old Billion-Dollar Fund Manager
Date: December 1, 2025
Guest: Eva Shang, Co-Founder & CEO of Legalist
Host: David Weisburd

Overview:

This episode dives into the unconventional trajectory of Eva Shang, the 29-year-old co-founder of Legalist, a billion-dollar fund and litigation finance platform. Eva recounts her journey from Harvard dropout and Thiel Fellow to leading a pioneering investment fund. The conversation unpacks her decision-making, approach to building enduring value, insights into the niche world of litigation finance and government receivables, and advice for aspiring institutional investors and founders who hope to play the long game in alternatives.

Key Discussion Points & Insights

1. Legalist’s Founding Story and Pivot to Litigation Finance

• (00:08-03:05):
  • Eva and her co-founder Christian started Legalist at Harvard in 2016, originally as a legal analytics startup.
  • Their idea was critiqued at Y Combinator:

    “Lawyers already know if their cases are dogs, and they don’t really care.” (Eva recounting John Levy, 00:42)

  • Pivoted after advice: leverage their proprietary case-level data to invest in litigation finance rather than only serving it to attorneys.
  • Entered litigation finance after contrasting it with insurance, noting the appealing "bird’s eye" market opportunity.

2. Choosing a Fund Structure Over a Fintech Originator Model

• (03:05-05:42):
  • Deliberately chose to become an asset manager—raising successive funds—instead of focusing purely on origination volumes (the VC-backed typical fintech path).
  • Eva emphasized the capacity-constrained nature of litigation finance—success depends on underwriting, not just volume:

    "The hallmark of a good asset manager is not volume of origination, but rather the IRR of your investments." (B, 04:21)

  • Avoided the unsustainable pressure of high-velocity deal flow in an illiquid, niche market.

3. Building Slow, Enduring Value

• (05:28-06:48):
  • David summarizes the need for compounding, saleable value:

    "In order to be a billionaire, you have to create 10 billion plus in value...and the only way...is to create sustainable, enduring value." (A, 05:45)

  • Eva reinforces: build patiently, don’t seek shortcuts like “the Adam Neumann route” (B, 06:38).

4. The Grit of Fundraising and Scaling AUM

• (07:03-08:29):
  • Underestimated the challenge of raising the first $10M fund—support from “a few people in the Valley willing to take a shot.”
  • Gradually grew from $10M to $100M, $300M, and now ~$1.5B AUM:

    “If I were looking at my own pitch deck from back then, I'd probably be like, I don’t really know about this...” (B, 07:57)

  • The first years were demoralizing—little visible progress compared to other startups.
  • Institutional credibility came with Fund 2 ($100M), enabling strategic growth (e.g., bankruptcy, mass torts, government receivables).

5. What LPs Really Care About

• (10:19-11:27):
  • Alpha matters, but repeatable process (“smart alpha”) matters more to institutional LPs.
  • Different LPs have different criteria:
    • Family offices = risk-takers, care more about the story.
    • Pension funds, OCs = process, org. controls, and policies.

6. Capacity-Constrained Asset Classes: Secrets to Alpha

• (11:27–13:31):
  • Litigation finance is “capacity constrained”—there are finite opportunities and capital cannot scale infinitely.
  • Alpha persists in such niches because markets don’t erase all inefficiencies:

    "A lot of strategies that generate super high alpha are capacity constrained because the purpose of a market is to erode alpha." (B, 12:39)

  • Large endowments don’t compete because the check sizes don’t fit.

7. Structure and Alpha of Litigation Finance

• (14:28–18:54):
  • Litigation finance originated as ATE (After the Event) insurance in Europe; in the US, it fits where there’s no attorney contingency.
  • Fills the “contingency gap” for large, complex litigation cases.
  • Legalist’s source of alpha: diversification through technology—a portfolio of 500+ cases, over 200 realizations.
  • Contrast: Early funds took concentrated risk, betting on single big cases (e.g., Burford’s Peterson claims).

    "Our thesis...was that we did not need to take such extreme concentration risk when we could instead use our algorithm..." (B, 18:19)

8. Government Receivables: Strategy Expansion

• (19:03–21:33):
  • University endowment LP requested exposure—Legalist built a tech-driven process to tap the market for short-duration, income-generating government receivables.
  • Received a $100M anchor commitment; expanded to allow 150+ additional investors due to visible success.

9. Contrarian Mindset and Long-Term Thinking in Youth

• (21:33–25:28):
  • David probes Thiel Fellows’ unusual patience and vision:

    "Some common examples, Dylan from Figma...didn't even launch until year five and he was in his teens." (A, 21:40)

  • Eva credits “not coveting what others covet” as core to the Thiel Fellowship spirit:

    "I think a lot of Thiel Fellows have that innate difference within them, which is that they do not covet what other people covet." (B, 23:45)

  • Not all contrarians are financially motivated; some value independence for its own sake.

10. Timeless Advice: The Value of People

• (25:28–26:21):
  • If Eva could advise her 18-year-old self, she’d highlight the importance of hiring and retaining great people—advice she initially dismissed as trite:

    “The secret to my success is to hire great people and to retain them. And I was like, oh my God, this is the most cliche, trite piece of advice... [but it] was the correct advice all along.” (B, 25:46)

  • Team quality is essential as the scale increases:

    “If you don’t have team cohesion and great people... there’s no way anything that’s larger than just yourself can get off the ground.” (B, 26:26)

Notable Quotes & Memorable Moments (with Timestamps)

• On Breaking Into Litigation Finance:

  “If you have that kind of bird’s eye view, why don’t you go into a field where you can actually make money off of it, such as litigation finance?” (B, recounting John Levy, 01:38)

• On Capacity Constrained Assets:

  "A capacity constrained asset class is an asset class that does not work if you put infinite money into it." (B, 11:39)

• On Creating Enduring Value:

  "You have to build a business that is worth something in year 10. That’s compounding and that has a multiple associated with it..." (A, 05:57)

• On Contrarian Motivation:

  “Roland Fryer... said it’s because I do not covet what they covet. And I think a lot of Thiel Fellows have that innate difference...” (B, 23:25)

• Advice to Her Younger Self:

  “Hire great people and retain them... It turns out that was the correct advice all along.” (B, 25:46)

Timestamps for Key Segments

• Founding & Early Pivot: 00:08–03:05
• Fund Structure Decision: 03:05–05:42
• Philosophy of Enduring Value: 05:42–06:48
• Fundraising & Scaling AUM: 07:03–08:29
• LP Mentality: 10:19–11:27
• Capacity-Constrained Assets Explained: 11:27–13:31
• Litigation Finance Structure & Alpha: 14:28–18:54
• Government Receivables Expansion: 19:03–21:33
• Thiel Fellows/Contrarian Mindsets: 21:33–25:28
• Timeless Advice: Build a Great Team: 25:28–26:21

Conclusion

This episode offers an unusual and honest look into the mindset, strategy, and processes behind building Legalist into a billion-dollar alternative asset manager. Eva’s approach—meticulous, contrarian, and grounded in long-term thinking—shows why some fund managers are able to compound value and scale in capacity-constrained, high-alpha alternatives.

For listeners:

• If you want to understand the real work behind the scenes in alternative asset management, the importance of capacity constraints, and the nuances of LP relationships and fund structure, this episode is essential listening.