Due Diligence Management as a Sleeper Pain Point

Why is up to “$150 trillion” poised to migrate from public to private markets—and what will unlock that shift for RIAs and family offices? In this episode, I examine that question with David Sawyer, CEO & Co-Founder of Unlimited.ai. We unpack the real blockers to alternatives adoption—operational, reporting, diligence, and liquidity complexity—and how AI can turn PDFs and siloed portals into queryable, decision-ready data for LPs. We talk RIA psychology, the GP/LP information asymmetry, and why solving “complexity” is the catalyst for the public-to-private transition cited by industry leaders (including the oft-quoted $150T prediction).

Highlights:

• Four kinds of complexity stopping alts adoption: access, legal/regulatory, reporting (K-1s, non-standard NAVs), and liquidity.
• Why operational complexity is the #1 reason many RIAs avoid alts (industry surveys ~40–50%).
• The public → private shift: volatility aversion + search for alpha and predictability.
• Information asymmetry has widened: trillion-dollar GPs vs. individuals and smaller RIAs—why tooling must level the field.
• AI’s role: extract, integrate, and chat with unstructured docs; unified LP workflow from access → diligence → reporting → exit.
• RIA reality: clients already bring outside deals/K-1s—consolidated balance-sheet reporting is now table stakes.
• Why due-diligence management is the sleeper pain point—and how comparative analytics change decisions
• Context for performance: the conversation references Kaplan–Schoar/PME research on PE vs. public markets (as discussed in-episode)

Guest Bio:

David Sawyer is CEO & Co-Founder of Unlimited.ai, an AI-native platform built to orchestrate LP workflows in private markets. Previously, he served as Managing Partner & COO at Legacy Knight, a multi-family office and alternatives platform, and as Managing Director at CAZ Investments. He holds a J.D. from the University of Houston Law Center, studied at the University of Texas at Austin, and is a CAIA charter holder.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

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LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ David Sawyer: https://www.linkedin.com/in/david-sawyer-a70ab912/

Links Unlimited.ai: https://www.unlimited.ai/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Introduction (2:54) The role of technology in alternative investment management (7:31) Strategies for overcoming operational complexity in private markets (10:21) AI's impact on investor access and information symmetry (22:07) Standardization and transparency in private market investments (23:06) Empowering investors with technology and community initiatives (23:56) Closing remarks