Shure's founders pivoted back to their original EOR concept, which failed years prior due to a lack of automation infrastructure. The recent maturity of AI agents and stablecoin rails made the initial vision feasible, showing that timing and technological readiness are critical for an idea's success.

The most successful venture investors share two key traits: they originate investments from a first-principles or contrarian standpoint, and they possess the conviction to concentrate significant capital into their winning portfolio companies as they emerge.

Many successful second-time founders don't innovate into new fields. Instead, they re-apply a proven playbook to the same market, much like a gamer "speed-running" a familiar level. This leverages deep domain expertise to execute faster and more effectively, bypassing the learning curve of a new industry.

True investment courage isn't just writing the first check; it's being willing to invest again in a category after a previous investment failed. Many investors become biased and write off entire sectors after a single bad experience, but enduring VCs understand that timing and team make all the difference.

A core part of a16z's growth fund strategy is to invest in companies the firm's early-stage team passed on. This acts as an internal "fix the mistake fund," providing a structured way to correct errors of omission and get a second chance at breakout companies.

An investor's best career P&L winners are not immediate yeses. They often involve an initial pass by either the investor or the company. This shows that timing and building relationships over multiple rounds can be more crucial than a single early-stage decision, as a 'missed round' isn't a 'missed company'.

Investors often reject ideas in markets where previous companies failed, a bias they call "scar tissue." This creates an opportunity for founders who can identify a key change—like new AI technology or shifting consumer behavior—that makes a previously impossible idea now viable.

The venture capital business requires consistent investment, not sprinting and pausing based on market conditions. A common mistake is for VCs to stop investing during downturns. For companies with 50-100x growth potential, overpaying slightly on entry price is irrelevant, as the key is capturing the outlier returns, not timing the market.

A truly exceptional founder is a talent magnet who will relentlessly iterate until they find a winning model. Rejecting a partnership based on a weak initial idea is a mistake; the founder's talent is the real asset. They will likely pivot to a much bigger opportunity.