Command Palette

Search for a command to run...

PodMine
Monetary Matters with Jack Farley
Monetary Matters with Jack Farley•September 16, 2025

Outperforming the S&P 500 & Growing from One-Man Shop to Multi-Manager Hedge Fund | David Orr of Militia Capital

A hedge fund manager shares insights on his journey from a one-man shop to a multi-manager fund, discussing investment philosophy, market perspectives, and navigating regulatory compliance.
Solo Entrepreneurs
Business News Analysis
Venture Capital
David Orr
Jason Chapayro
Ian Bezek
Matt Stewart
VanEck

Summary Sections

  • Podcast Summary
  • Speakers
  • Key Takeaways
  • Statistics & Facts
  • Compelling StoriesPremium
  • Thought-Provoking QuotesPremium
  • Strategies & FrameworksPremium
  • Similar StrategiesPlus
  • Additional ContextPremium
  • Key Takeaways TablePlus
  • Critical AnalysisPlus
  • Books & Articles MentionedPlus
  • Products, Tools & Software MentionedPlus
0:00/0:00

Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.

0:00/0:00

Podcast Summary

David Orr, founder and CIO of Militia Capital, discusses transforming his $160 million long-short equity hedge fund into a multi-manager platform. Starting with just $3 million in 2021, the fund has grown primarily through profits rather than capital raises. (01:57) Orr explains his unique approach to finding uncorrelated portfolio managers and his willingness to speak openly on social media despite industry conventions.

  • Main themes include multi-manager hedge fund evolution, social media transparency in finance, and contrarian investment philosophy focused on balance sheet analysis over popular narratives.

Speakers

David Orr

David Orr is the founder and CIO of Militia Capital, a hedge fund that launched in 2021 with $3 million and has grown to $160 million in assets under management. He has a background in poker which influences his risk management approach and portfolio manager selection process. Orr is known for his active presence on finance Twitter and his contrarian investment philosophy focused on balance sheet analysis and short selling.

Key Takeaways

Focus on Balance Sheet Analysis Over Popular Narratives

Many investors, particularly self-described value investors, fail to properly analyze balance sheets and capital structures. (33:40) Orr emphasizes that you can have a reasonable operating business, but if it's sitting behind massive debt or lease liabilities, the equity can become worthless quickly. This fundamental analysis is often ignored by both value investors who focus solely on price multiples and story stock investors who rely purely on sentiment and momentum.

Embrace Regulatory Clarity Through Direct Research

Rather than relying on overly conservative compliance professionals, Orr advocates for reading actual regulations yourself. (06:27) He discovered that many compliance restrictions were interpretations rather than actual legal requirements. By using the 506(c) exemption instead of the more restrictive 506(b), he gained significant marketing flexibility while still maintaining proper investor accreditation verification.

Build Uncorrelated Portfolio Manager Relationships

Successful multi-manager platforms require finding portfolio managers with different styles and geographic focuses to maintain low correlation. (49:01) Orr specifically seeks quirky thinkers who operate outside conventional frameworks, and he's particularly interested in long-short bond and biotech specialists. The key is understanding their risk-taking patterns while allowing them significant autonomy.

Recognize Market Exhaustion Through Breadth Analysis

During speculative rallies, watch for correlation breakdown among momentum stocks as a signal of impending reversal. (39:48) Orr explains that when speculative money spreads from epicenter stocks to broader junk names, and then correlation dies down before prices fall, it indicates the market has spread to too much speculative content with no remaining dry powder.

Maintain Tax Efficiency as a Competitive Advantage

Tax loss harvesting and holding long positions for extended periods can provide significant alpha, especially with primarily US-based taxable investors. (22:01) Orr regularly harvests tax losses on short positions by closing them and reopening after 30 days, while holding quality longs for years to capture the tax advantage of long-term capital gains treatment.

Statistics & Facts

  1. Militia Capital grew from $3 million at launch in 2021 to $160 million in assets under management, with David Orr noting that most growth came from profits rather than capital raises. (01:47)
  2. The fund currently holds over 1,000 positions across its multi-manager structure, resulting in volatility that is now lower than the S&P 500, compared to nearly double the S&P 500's volatility when Orr was the sole manager. (12:09)
  3. Orr's personal partition within the fund grew from $10 million in net deposits to $90 million, meaning approximately $60-70 million went to support other portfolio managers, primarily funded from his own profits. (04:00)

Compelling Stories

Available with a Premium subscription

Thought-Provoking Quotes

Available with a Premium subscription

Strategies & Frameworks

Available with a Premium subscription

Similar Strategies

Available with a Plus subscription

Additional Context

Available with a Premium subscription

Key Takeaways Table

Available with a Plus subscription

Critical Analysis

Available with a Plus subscription

Books & Articles Mentioned

Available with a Plus subscription

Products, Tools & Software Mentioned

Available with a Plus subscription

More episodes like this

The Prof G Pod with Scott Galloway
January 14, 2026

Raging Moderates: Is This a Turning Point for America? (ft. Sarah Longwell)

The Prof G Pod with Scott Galloway
Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)
January 14, 2026

The Productivity Framework That Eliminates Burnout and Maximizes Output | Productivity | Presented by Working Genius

Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)
On Purpose with Jay Shetty
January 14, 2026

MEL ROBBINS: How to Stop People-Pleasing Without Feeling Guilty (Follow THIS Simple Rule to Set Boundaries and Stop Putting Yourself Last!)

On Purpose with Jay Shetty
Tetragrammaton with Rick Rubin
January 14, 2026

Joseph Nguyen

Tetragrammaton with Rick Rubin
Swipe to navigate