Unlike traditional software that optimizes for time-in-app, the most successful AI products will be measured by their ability to save users time. The new benchmark for value will be how much cognitive load or manual work is automated "behind the scenes," fundamentally changing the definition of a successful product.
Echoing the Hippocratic Oath, a venture investor's primary job with a high-performing company is to stay out of the way and not disrupt its momentum. While providing resources for talent, capital, and strategy is valuable, it's secondary to the core principle of not interfering with a team that is already executing successfully.
Shopify's evolution shows that initial TAM estimates can be conservative. By strategically expanding into adjacent "horizons" like payments, companies can "add a zero" to their market opportunity. This justifies long-term growth and high valuations, a lesson Bessemer now applies to its portfolio.
The hardest transition from entrepreneur to investor is curbing the instinct to solve problems and imagine "what could be." The best venture deals aren't about fixing a company but finding teams already on a trajectory to succeed, then helping change the slope of that success line on the margin.
Bessemer Venture Partners publicly lists massive companies it passed on to foster a learning culture. This highlights their philosophy that the opportunity cost of missing a transformative company (a crime of omission) is far more damaging than investing in one that fails (a crime of commission).
Bessemer's investment process favors individual partner conviction over group consensus. A partner can "pound the table" for a deal (the "gold nugget") without the risk of another partner vetoing it (the "blackball" model). This fosters ownership and bold bets, with performance as the ultimate accountability.
In dynamic markets like AI, where technology and business models evolve rapidly, the founding team's quality ('the jockey') becomes more critical than the initial business plan ('the horse'). The ability of a small, talented team to pivot and execute on new opportunities is the key determinant of success.