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.

Notion's funding history reveals its valuation significantly outpaced revenue, reaching $10B on just $31M ARR in 2021. However, the company subsequently grew revenue almost 20x to $600M while its valuation only increased 10%, demonstrating how outlier companies can eventually grow into seemingly inflated valuations.

An investor passed on a fund that paid 30-40x revenue for startups, believing quality alone justifies price. Three years later, that fund and its predecessors are underwater. This illustrates that even for great companies, undisciplined entry valuations and the assumption of multiple expansion can lead to poor returns.

Investing in a high-growth company like ClickHouse at a $15B valuation isn't complex; it's a direct bet on "growth persistence." The entire financial model hinges on the assumption that the recent, extreme growth rate will continue for another 2-3 years. Any premature deceleration invalidates the entry price.

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.

Chasing high, unrealized valuations is dangerous. It makes common stock prohibitively expensive, undermining the potential for life-changing wealth for employees—a key recruiting tool. It also narrows a company's strategic options, locking it into a high-stakes path where anything less than exceeding the last valuation is seen as failure.

To generate returns on a $10B acquisition, a PE firm needs a $25B exit, which often means an IPO. They must underwrite this IPO at a discount to public comps, despite having paid a 30% premium to acquire the company, creating a significant initial value gap to overcome from day one.

The market has fundamentally reset how it values mature SaaS companies. No longer priced on revenue growth, they are now treated like industrial firms. The valuation bottom is only found when they trade at free cash flow multiples that fully account for stock-based compensation.