Deep Due Diligence, AI Deal Screening & Private Investing | Marc Halpern Fireside Chat

In this episode of The Capital Raiser Show, Richard C. Wilson sits down with Marc Halpern, co-founder of the Deep Due Diligence Investors Club, for a fireside chat on screening private placements at scale, managing risk in alternative investments, team-based due diligence, and what separates disciplined investors from everyone else.

Marc shares lessons from five decades of breakthrough R&D and private investing, including the "jockey, horse, and track" framework, how his club uses AI to screen 400+ deals a year in seconds, and why reading every word of a PPM is still non-negotiable.

The conversation dives into deal screening discipline, portfolio strategy, diversification, stress testing sponsors through market cycles, and how a team of 58 investors from wildly different professional backgrounds covers each other's blind spots better than any single expert could.

Topics covered include:

The "jockey, horse, and track" framework for evaluating any deal

How AI deal screening tools cut through hundreds of opportunities in seconds

Deep due diligence in teams and why diverse professional backgrounds matter

Minimizing risk vs. eliminating it - and why you can only do one

Portfolio strategy before individual investment selection

Diversification vs. de-worsification and finding the right balance

Stress testing sponsors through the Fed rate cycle of 2022-2023

When to walk away quickly and take no for an answer