Instead of fighting incumbents for their entrenched "hostage" customers, startups should focus on "Greenfield Bingo." This strategy involves building a better product and selling it to the steady stream of new companies that are not yet locked into a solution. This approach thrives in markets with high rates of new business formation.
A common trait among exceptional founders is a deep, almost academic, understanding of their industry's history. They learn from every past attempt, success, and failure. This historical context allows them to innovate with a unique perspective and avoid the pitfalls that doomed their predecessors, a sign of true commitment and expertise.
While capital is necessary, an overabundance is dangerous. Large secondaries can make founders comfortable and misaligned with investors. Excessive primary capital leads to bloat, unfocused strategy, and removes the pressure that drives invention. This moral hazard often leads to worse outcomes than being capital-constrained.
The most defensible businesses, especially in enterprise software, create such high switching costs that customers are essentially locked in. This "hostage" dynamic, where leaving is prohibitively difficult, is a stronger moat than simply having satisfied customers who could still churn. It's the foundation of an enduring software business.
In venture capital, mid-sized generalist funds struggle to compete. They lack the scale and network of large generalists and the deep expertise of small specialists. This 'death of the middle' makes it difficult for them to win the best, most competitive deals against firms that can offer either breadth or depth.
Founders who wait until they need to sell have already failed. A successful exit requires a multi-year 'background process' of building relationships. The key is to engage with SVPs and business unit leaders at potential acquirers—the people who will champion the deal internally—not just the Corp Dev team who merely execute transactions.
Financial motivation has a ceiling. Once a founder is offered life-changing money, only a deeper drive will push them forward. The best entrepreneurs often have a chip on their shoulder—a desire for revenge against a former rival or redemption for a past failure. This "Count of Monte Cristo" motivation is essential for building massive, enduring companies.
The most investable founders possess a rare, magnetic ability to conjure essential resources. They can convince top talent to take pay cuts, persuade investors to fund an unproven vision, and acquire their first crucial customers against all odds. This trifecta of materializing labor, capital, and customers is a powerful leading indicator of success.
Accepting too high a valuation can be a fatal error. The first question in any subsequent fundraising or M&A discussion will be about the prior round's price. An unjustifiably high number immediately destroys the psychology of the new deal, making it nearly impossible to raise more capital or sell the company, regardless of progress.
Beyond product-market fit, there is "Founder-Capital Fit." Some founders thrive with infinite capital, while for others it creates a moral hazard, leading to a loss of focus and an inability to make hard choices. An investor's job is to discern which type of founder they're backing before deploying capital that could inadvertently ruin the company.
Traditional valuation doesn't apply to early-stage startups. A VC investment is functionally an out-of-the-money call option. VCs pay a premium for a small percentage, betting that the company's future value will grow so massively that their option expires 'in the money.' This model explains high valuations for pre-revenue companies with huge potential.
A universal ownership target is flawed. The strategy should adapt to a company's traction. For rare, breakout companies with undeniable product-market fit ('absolutely working'), a VC should take any stake they can get. For promising but unproven ideas ('could work'), they must secure high ownership to compensate for the greater risk.