Once a clear buy signal for investors, large-scale share repurchases now often indicate that a company with a legacy moat has no better use for its cash. This can be a red flag that its core business is being disrupted by new technology, as seen with cable networks and department stores.

Identifying a stock trading below its intrinsic value is only the first step. To avoid "value traps" (stocks that stay cheap forever), investors must also identify a specific catalyst that will unlock its value over a reasonable timeframe, typically 2-4 years.

Canadian retailer Leon's Furniture holds a valuable real estate portfolio, including prime development land, on its books for a fraction of its market value. A plan to IPO this real estate into a REIT creates a clear catalyst to unlock this hidden value, a common playbook for scaled Canadian retailers.

Unlike scalable digital businesses, real estate has a hard ceiling on returns. You can't innovate on a property to dramatically increase revenue without massive capital expenditure. This lack of operational leverage limits its upside compared to businesses where profits can be reinvested into growth initiatives.

Aggregate profitability can mask serious issues. A company's positive bottom line might be propped up by one highly profitable offer while another "bestseller" is actually losing money on every sale. This requires a granular, per-product profitability analysis to uncover.

Citing Bed Bath & Beyond as a cautionary tale, the speaker warns against being lured by share buybacks in companies with declining fundamentals. A cheap valuation and aggressive repurchases cannot save a business that is fundamentally broken, a lesson he applies to the situation at Charter Communications.

Corporate leaders are incentivized and wired to pursue growth through acquisition, constantly getting bigger. However, they consistently fail at the strategically crucial, but less glamorous, task of divesting assets at the right time, often holding on until value has significantly eroded.

WeWork created "Community Adjusted EBITDA," a metric that conveniently excluded core costs like rent and salaries. This farcical KPI incentivized top-line growth at any cost, masking massive unprofitability and ultimately destroying shareholder value. Be wary of overly creative accounting.

Instead of labeling a potential issue like negative cash flow as a definitive "red flag," which can be misleading, view it as a "flammable item." By itself, it may be harmless. The real danger only materializes when a "spark"—a catalyst like a new competitor or rising interest rates—is introduced.