Investors like Stacy Brown-Philpot and Aileen Lee now expect founders to demonstrate a clear, rapid path to massive scale early on. The old assumption that the next funding round would solve for scalability is gone; proof is required upfront.
Investors like Reid Hoffman see the fundraising negotiation not as a zero-sum game, but as a crucial test of a founder's character, realism, and suitability as a long-term partner. Unreasonable or unrealistic demands, even in a hot deal, are a negative signal that can kill an investment.
Periods of intense technological disruption, like the current AI wave, destabilize established hierarchies and biases. This creates a unique opportunity for founders from non-traditional backgrounds who may be more resilient and can identify market needs overlooked by incumbents.
Raising too much money at a high valuation puts a "bogey on your back." It forces a "shoot the moon" strategy, which can decrease capital efficiency, make future fundraising harder, and limit potential exit opportunities by making the company too expensive for acquirers.
Instead of walking into a pitch unprepared, Reid Hoffman advises founders to use large language models to pre-emptively critique their business idea. Prompting an AI to act as a skeptical VC helps founders anticipate tough questions and strengthen their narrative before meeting real investors.
Investor Stacy Brown-Philpot advises that to win large enterprise deals, an AI startup must create a solution so compelling it beats the customer's internal team vying for the same budget. The goal is to access the core 15% budget pool, not the 1% 'play money' budget.