Episode
Episode 386: Is anyone doing dd? with Aravind Sithamparapillai
- Published
- Dec 4, 2025
- Duration seconds
- 4567
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Summary
What happens when alternative investments shift from niche products to the industry's go-to value proposition? In this episode, we're joined by financial planner and self-described "pathological nerd" Aravind Sithamparapillai for a rigorous exploration of private markets, product due diligence, advisor incentives, and the narratives driving the surging popularity of alts. Aravind has become known in advisor circles for asking the uncomfortable questions at conferences—the ones that expose gaps in explanations, shaky assumptions, and in some cases, outright contradictions. In this conversation, he shares the stories and analytical frameworks behind his deep dives into mortgage funds, private credit, private real estate, IRR-based marketing, vintage stacking, stale pricing, operational risk, and why even large professional allocators get burned. We explore how advisors are selling alts, how funds are pitching them, what due diligence actually requires, how expected returns can be decomposed, and why illiquidity and "low correlation" benefits rarely play out in practice. Aravind also explains how some funds maintain stable NAVs through "extend and pretend," how gating works, why audited financials aren't a safety blanket, and why even top-tier firms miss red flags. Key Points From This Episode: (0:00:38) Aravind's introduction and reputation for deep, "pathological" research (0:02:23) Why alts have become embedded in Toronto's planning culture (0:03:38) Client pressure, advisor FOMO, and the belief that 60/40 is "broken" (0:05:31) Aravind's personal path into indexing, factors, and Dimensional (0:10:46) Why he started digging into alts: curiosity, client conversations, and advisor narratives (0:13:47) The "conference meme": why he asks questions others avoid (16:58) The r…