Counter-cyclical fundraising is powerful. When capital is scarce, the herd mentality subsides, reducing competition and allowing savvy investors and founders to secure better opportunities and terms. It's a contrarian approach that capitalizes on market lows when others are fearful.

Marks frames contrarian investing not as simple opposition, but as using the market's excessive force (optimism or pessimism) against itself. This mental model involves letting the market's momentum create opportunities, like selling into euphoric buying, rather than just betting against the crowd.

The best moments to buy are created by widespread fear and bad news, making you instinctively not want to. A great investor isn't someone who is unafraid during these times; they are someone who acts rationally despite the overwhelming emotional pressure to sell or stay on the sidelines.

During a crisis, avoid the temptation to trade based on predictions of how events will unfold. Instead, use the market volatility to purchase pre-identified, resilient companies at better prices, accelerating your existing strategy rather than creating a reactive new one.

During COVID, the market priced Booking.com as if travel would never recover. The investment thesis was based on historical precedent (e.g., SARS) showing that travel disruptions are typically brief. This counter-consensus view on the duration of the downturn led to a highly profitable investment.

Marks advises that the greatest investment opportunities appear during market crashes when the news is terrible. Waiting until you have "nothing to be afraid about" means the opportunity has already passed. True investors must act despite their fear and trepidation.

Instead of using prediction markets or pure gambling, a more strategic way to speculate on future events is to invest in related physical assets. For example, buying a player's trading card is an investment that can appreciate based on an outcome, like a team winning a championship, turning a bet into an asset purchase.

Hetty Green's famous strategy to "buy when things are low" was enabled by two key factors: always having cash on hand and possessing the emotional stability to act decisively when others were panicking. Having liquidity is useless without the courage to deploy it during a crisis, a combination few possess.

The best investment deals are not deeply discounted, low-quality items like "unsellable teal crocodile loafers." Instead, they are the rare, high-quality assets that seldom come on sale. For investors, the key is to have the conviction and preparedness to act decisively when these infrequent opportunities appear.