Cannabis Investing Network · CIN Podcast

#219 - The Golden Age of Stock Picking, Volatility & Opportunity (ft. Scott Grossman of Turning Point Brands)

March 18, 2026·1 hr 36 min·5 clips

Retail investors can take risks professionals can't because they don't have to answer to boards or fear job loss.

This episode of the Cannabis Investing Network explores market volatility and strategic investing in a rapidly changing world. Host Manish is joined by returning guest Scotty "SRG444" Grossman, an investor and operator with Turning Point Brands who brings over 25 years of market experience. Grossman emphasizes that understanding transformational trends requires looking beyond one's immediate focus. A central theme is Grossman's concept of "watching the periphery," which he defines as maintaining situational awareness by observing edges and adjacent sectors to inform core decisions. He argues we are in a period of "time compression," where market shocks and recoveries happen faster, evidenced by the Volatility Index (VIX). Grossman notes specific VIX spikes: Volmageddon in 2018, COVID-19 in 2020, Silicon Valley Bank in 2024, a yen carry trade event, and the recent "tariff tantrum." He contrasts the 50% peak-to-trough decline and seven-year recovery from the dot-com bubble with the 20% decline and seven-week recovery from the tariff tantrum. Grossman and Manish discuss how over 80% of equity flows are now programmatic, driven by algorithms at firms like Citadel and Jane Street, leading to synchronized sell-offs. Manish shares an anecdote about a fund manager who identified a compelling office deal but was constrained from investing due to board and shareholder expectations. The conversation highlights how retail investors, unlike professionals, can act on niche opportunities without such constraints. A surprising insight is that actionable investment "alpha" now often originates on platforms like Twitter and Substack rather than traditional financial media. Manish cites an example where a hypothetical Substack article about AI's impact on software by Citrini coincided with a market dip initially misattributed by CNBC to tariff news. Grossman asserts that professionals at investment banks and sell-side firms are often hindered because they are not fully utilizing AI tools daily. He believes the accelerating pace of change, exemplified by AI, makes human specialization a potential liability, as experts can become siloed. Manish recounts a story from a friend building AI agents for a private equity firm, demonstrating how AI can make it easier for companies to switch off legacy software systems like Salesforce by creating more intuitive interfaces. Grossman connects this to a broader "software slop" thesis, questioning the durability of software moats built over time when AI can now replicate solutions quickly. The episode has an educational and conversational tone, blending market analysis with practical anecdotes and specific examples. Investors interested in tactical stock picking, understanding macro volatility, and leveraging non-traditional information sources will find this episode valuable. Listeners seeking a passive, long-term investment approach or those uncomfortable with rapid market narratives may find the content less relevant.

As heard by us

A wide market conversation about stock picking, AI, and whether software moats still hold.

Cannabis Investing Network opens with a plain case for stock picking in a market that feels shaky, and it keeps coming back to whether old assumptions still hold.

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Want a market debate that treats volatility as opportunity?

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