Raise capital when you can clearly see upcoming growth and need resources to service it. Tying your timeline to operational milestones, like onboarding new customers, creates genuine urgency and momentum. This drives investor FOMO and helps close deals more effectively than an arbitrary deadline.

The founder classifies fundraising into six buckets: finding PMF, funding growth, employee liquidity, trust/publicity, strategic partnerships, or ego. This framework helps founders avoid raising capital for momentum's sake, which often adds unnecessary risk and dilution.

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.

For startups experiencing hyper-growth, the optimal strategy is to raise capital aggressively and frequently—even multiple times a year—regardless of current cash reserves. This builds a war chest, solidifies a high valuation based on momentum, and effectively starves less explosive competitors of investor attention and capital.

Raising venture capital is often a network-driven game. If you don't already have a network of VCs or a clear path through an accelerator, your focus should not be on fundraising. Instead, dedicate your effort to building a product people want and gaining traction. VCs will find you once you have something compelling to show.

Market dynamics are not static. What was once a 'wave'—a new, urgent problem for everyone—can evolve into a series of 'dams' and eventually a stable 'river.' A common mistake is to build for the hype of a wave after it has crested, by which point it no longer provides the same opportunity for explosive growth.

When sales stall, founders assume the market isn't interested. More often, it's an execution problem: they fail to listen to clear demand signals or pitch irrelevant features, creating a self-inflicted "demand problem."