There is an inverse relationship between a portfolio company's performance and the time it demands from a VC. The breakout winners (the top 5%) often require minimal oversight, while struggling companies consume the most time and energy. This is a critical lesson in time allocation for investors.
The journey of any successful startup is not a straight line; it inevitably includes multiple moments where the company faces existential threats. Understanding and normalizing this reality from the beginning helps founders and investors frame their relationship as a long-term partnership built to withstand extreme volatility.
In VC, where being wrong is the norm (80%+ of the time), the most critical trait is not righteousness but deep curiosity. This learning-first mindset is what uncovers non-obvious opportunities and allows investors to see future market shifts before they become mainstream, according to True Ventures' Jon Callaghan.
Historical tech cycles like the cloud and mobile demonstrate a consistent pattern: the application layer ultimately generates 5 to 10 times the value of the underlying infrastructure capital expenditure. With trillions being invested in AI infrastructure, future value creation at the application layer will be astronomically larger.
By defining the entrepreneur as the primary customer, a VC firm changes its entire operating model. This customer-centric view informs decisions on partner incentives (removing attribution), community building, and support services. The result is a powerful brand that attracts the best founders and generates high-fidelity deal flow through referrals.
While first-time founders often optimize for the highest valuation, experienced entrepreneurs know this is a trap. They deliberately raise at a reasonable price, even if a higher one is available. This preserves strategic flexibility, makes future fundraising less perilous, and keeps options open—which is more valuable than a vanity valuation.
The biggest venture outcomes often take 8-10 years or more to mature. Instead of optimizing for quick IRR, early-stage VCs should embrace long holding periods. This "duration" is a feature that allows for massive value creation and aligns with building truly transformative companies, prioritizing multiples over short-term gains.
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.
A successful early-stage strategy involves actively maximizing specific risks—product, market, and timing—to pursue transformative ideas. Conversely, risks related to capital efficiency and team quality should be minimized. This framework pushes a firm to take big, non-obvious swings instead of settling for safer, incremental bets.
The media's obsession with a few dozen AI mega-rounds creates a distorted view of the early-stage market. Data shows that of the ~1,500 seed deals done per quarter, the vast majority remain within traditional parameters ($1-5M checks, sub-$30M valuations). Founders and investors should ignore the headline noise.