In venture capital, an investor's reputation is constantly on the line. A successful exit in one fund doesn't satisfy the LPs of a subsequent fund. This creates relentless pressure to consistently perform, as you're only as good as your last hit and can never rest on past achievements.

A venture capitalist's career security directly impacts the founder relationship. VCs with a proven track record (like Sequoia's Andrew Reed) act as supportive partners. In contrast, junior or less successful VCs often transfer pressure from their own partnerships onto the founder, creating a stressful and counterproductive dynamic.

New VCs often rush to make deals to prove themselves, but this leads to a portfolio of mediocre companies. These investments consume a disproportionate amount of time and energy, leaving no bandwidth to pursue the truly exceptional, career-making opportunities that may appear later.

The seed investing landscape isn't just expanding; it's actively replacing its previous generation. Legacy boutique seed firms are being squeezed by large multistage funds and new emerging managers, implying a VC's relevance has a 10-15 year cycle before a new cohort takes over.

Despite perceptions of quick wealth, venture capital is a long-term game. Investors can face periods of 10 years or more without receiving any cash distributions (carry) from their funds. This illiquidity and delayed gratification stand in stark contrast to the more immediate payouts seen in public markets or big tech compensation.

IVP's Samesh Dash observes that young VCs, driven by insecurity, often overcompensate by talking too much and offering premature advice. Maturing as an investor means shifting from talking to active listening, asking fewer but more pointed questions, and understanding a founder's immediate context before offering input.

The ideal period for venture investment—after a company is known but before its success becomes obvious—has compressed drastically. VCs are now forced to choose between investing in acute uncertainty or paying massive, near-public valuations.

The career arcs of venture and buyout investors differ starkly. VCs rely on networks relevant to young founders, leading some to retire by 45 as connections become stale. In contrast, buyout investing is an apprenticeship business where age and experience are increasingly valued.

The institutionalization of venture capital as a career path changes investor incentives. At large funds, individuals may be motivated to join hyped deals with well-known founders to advance their careers, rather than taking on the personal risk of backing a contrarian idea with higher return potential.