The ideal time to invest in an up-and-coming neighborhood isn't at the very beginning. Wait for tangible signals that the trend is real, such as new coffee shops or when ~25% of homes are renovated. This strategy confirms momentum while still capturing significant upside before the area fully turns.

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Contrary to the 'get in early' mantra, the certainty of a 3-5x return on a category-defining company like Databricks can be a more attractive investment than a high-risk seed deal. The time and risk-adjusted returns for late-stage winners are often superior.

Luxury properties with obvious but superficial flaws, like bad lighting or cheap finishes from a poor flip, can deter less-savvy buyers. This creates an opportunity to purchase a property well below its potential market value, as the cost to fix the flaws is often minimal compared to the value added.

Act like an investor with your time by forming hypotheses about which industries are most likely to experience your key compelling events. By predicting where M&A or new market entries will occur (e.g., in telecom), you can proactively focus your territory on high-probability accounts before events are announced.

Counterintuitively, the best multifamily markets aren't high-population-growth cities like Austin. These attract too much new supply, capping rent growth. The optimal strategy is to find markets with barriers to entry and minimal new construction, as this creates a durable runway for rental increases.

Don't chase every deal. Like a spearfisherman, anchor in a strategic area and wait patiently for the 'big fish'—a once-in-a-decade opportunity—then act decisively. This requires years of preparation and the discipline to let smaller opportunities pass by, focusing only on transformative deals.

Many LPs focus solely on backing the 'best people.' However, a manager's chosen strategy and market (the 'neighborhood') is a more critical determinant of success. A brilliant manager playing a difficult game may underperform a good manager in a structurally advantaged area.

A mix of old and new buildings is crucial for a vibrant neighborhood. Because new construction is expensive, it drives up rents, excluding smaller businesses and lower-income residents. Older buildings provide the affordable spaces necessary to foster a diverse economic and social ecosystem.

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.

General market conditions are less important than the specifics of an individual property. Making a good or bad purchase is possible in any market, so advice that ignores the particular deal is worthless. Success hinges on analyzing the property, not just the economic forecast.

Instead of predicting short-term outcomes, focus on macro trends that seem inevitable over a decade (e.g., more e-commerce, more 3D interaction). This framework, used by Tim Ferriss to invest in Shopify and by Roblox for mobile, helps identify high-potential areas and build with conviction.