A huge Series A before clear product-market fit creates immense pressure to scale prematurely. This can force 'unnatural acts' and unrealistic expectations, potentially leading the company to implode. It challenges the 'more money is always better' mindset at the early stages.

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.

When founders cash out millions early, it can create a disconnect. They become rich while their team and investors are not, which can reduce their hunger and create a 'moral hazard.' The motivation may shift from building a generation-defining company to preserving their newfound wealth.

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.

David Cohen observes that founders who are inherently frugal or "stingy" with capital—spending only when absolutely necessary—often achieve better outcomes. This mindset, focused on capital preservation and efficiency, is a more powerful indicator of success than simply raising large rounds to fuel growth, a trait he has seen in his own entrepreneurial career.

Chet Pipkin advises that a lack of cash is not always a bad thing for a new venture. Financial constraints force founders to focus on the essential aspects of their business and identify a genuine, pressing customer problem, which is more critical for success than having abundant capital.

A frequent conflict arises between cautious VCs who advise raising excess capital and optimistic founders who underestimate their needs. This misalignment often leads to companies running out of money, a preventable failure mode that veteran VCs have seen repeat for decades, especially when capital is tight.

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?'

Reflecting on raising $35M, Ergatta's founder suggests taking less capital might have been wiser. While tempting to raise as much as possible, large funding rounds lock the company into a specific financial trajectory and set of expectations. Raising less money can preserve crucial optionality and flexibility for the business's future.