Investing Experts

Investing in small caps with courage and conviction

12 snips
Sep 22, 2025
Courage & Conviction Investing, the founder of Second Wind Capital, dives deep into the fascinating world of high-conviction small- and micro-cap investing. He shares a philosophical take on his investment strategies, discussing the promising yet challenging positions in Green Plains and Cineverse. The conversation shifts to the impact of tariffs, macro uncertainties, and contrasts the small-cap space with AI-driven mega-cap momentum. Engaging insights on navigating market realities and prioritizing life alongside investing make this discussion a treasure for investors.
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ANECDOTE

Personal Context Shapes Investment Perspective

  • At 45, Second Wind Capital reflected on family, hospice visits, and busy sports seasons shaping perspective on markets.
  • He described a large April drawdown and the humbling grind of investing small caps this year.
INSIGHT

AI CapEx Creates Concentrated Market Momentum

  • AI capex drives massive flows into companies directly tied to that spend, inflating valuations and momentum.
  • Small-cap microcap universes often miss those flows, creating divergent performance versus large-cap AI beneficiaries.
ANECDOTE

Green Plains: Research, Drawdown, Recovery

  • He researched Green Plains deeply and misjudged inventory and seasonal ethanol margins, causing a large drawdown.
  • He stayed engaged with management, added in the lows, and later recovered significant gains as legislation and strategic changes helped margins.
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