Since startups lack infinite time and money, an investor's key diligence question is whether the team can learn and iterate fast enough to find a valuable solution before resources run out. This 'learning velocity' is more important than initial traction or a perfect starting plan.
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.
Moving from a science-focused research phase to building physical technology demonstrators is critical. The sooner a deep tech company does this, the faster it uncovers new real-world challenges, creates tangible proof for investors and customers, and fosters a culture of building, not just researching.
Diller’s process for navigating the unknown isn't about brilliance but relentless iteration. He describes it as taking "one dumb step" at a time, bouncing off the walls of bad ideas and mistakes, and course-correcting. This embraces looking foolish as a prerequisite for finding the right path.
Bootstrapping is often a capital constraint that limits a founder's full potential. Conversely, venture capital removes this constraint, acting as a forcing function that immediately reveals a founder's true capabilities in recruiting, product, and fundraising. It's the equivalent of 'going pro' by facing the raw question: 'How good am I?'
The number one reason founders fail is not a lack of competence but a crisis of confidence that leads to hesitation. They see what needs to be done but delay, bogged down by excuses. In a fast-moving environment, a smart decision made too late is no longer a smart decision.
The motivation to start a company wasn't about a guaranteed outcome but about embracing the ultimate test of one's capabilities. The realization that most founders, regardless of experience, are figuring it out as they go is empowering. It reframes the founder journey from a path for experts to a challenge for the determined.
While moats like network effects and brand develop over time, the only sustainable advantage an early-stage startup has is its iteration speed. The ability to quickly cycle through ideas, build MVPs, and gather feedback is the fundamental driver of success before achieving scale.