Cisco's stock took 25 years to reclaim its year-2000 peak, despite the underlying business growing significantly. This serves as a stark reminder that even a successful, growing company can deliver zero returns for decades if an investor buys in at an extremely high, bubble-era valuation.

When a company's valuation is based on profits projected decades into the future, it reaches a critical point. Investors eventually stop buying into even more distant projections, causing a stall as they wait for reality to catch up or sell to others who still believe.

Counter to conventional value investing wisdom, a low Price-to-Earnings (P/E) ratio is often a "value trap" that exists for a valid, negative reason. A high P/E, conversely, is a more reliable indicator that a stock may be overvalued and worth selling. This suggests avoiding cheap stocks is more important than simply finding them.

Before concluding a company can sustain extraordinary growth, consult historical data ('base rates') on how many similar companies succeeded in the past. This 'outside view,' a concept from investor Michael Mauboussin, provides a crucial reality check against overly optimistic forecasts.

Companies like Tesla and Oracle achieve massive valuations not through profits, but by capturing the dominant market story, such as becoming an "AI company." Investors should analyze a company's ability to create and own the next compelling narrative.

Traditional valuation multiples are increasingly misleading because GAAP rules expense intangible investments (R&D, brand building) rather than capitalizing them. For a company like Microsoft, properly capitalizing these investments can drop its P/E ratio from 35 to 30, revealing a more attractive valuation.

The standard VC heuristic—that each investment must potentially return the entire fund—is strained by hyper-valuations. For a company raising at ~$200M, a typical fund needs a 60x return, meaning a $12 billion exit is the minimum for the investment to be a success, not a grand slam.

Anchoring valuation on a company's typical price-to-sales ratio helps identify buying opportunities when margins are temporarily depressed. This avoids the pitfalls of methods like the Magic Formula, which can mistakenly favor companies at their cyclical earnings peaks, leading to underperformance.

High SaaS revenue multiples make buyouts too expensive for management teams. This contrasts with traditional businesses valued on lower EBITDA multiples, where buyouts are more common. The exception is for stable, low-growth SaaS companies where a deal might be structured with seller financing.