A company with over $9M ARR was initially ignored by investors because it didn't fit the typical early-stage YC profile. Once its revenue was revealed at Demo Day, it became the hottest deal, showing that non-traditional, more mature companies in YC can be overlooked champions.

The current fundraising environment is the most binary in recent memory. Startups with the "right" narrative—AI-native, elite incubator pedigree, explosive growth—get funded easily. Companies with solid but non-hype metrics, like classic SaaS growers, are finding it nearly impossible to raise capital. The middle market has vanished.

Startups in social impact or wellness often receive positive but misleading feedback from VCs. Investors are hesitant to reject these missions outright, so they offer praise while privately declining due to perceived weak business models and a lack of "cutthroat" founders. This creates a "Save the Whales trap" for idealistic entrepreneurs.

An investor's best career P&L winners are not immediate yeses. They often involve an initial pass by either the investor or the company. This shows that timing and building relationships over multiple rounds can be more crucial than a single early-stage decision, as a 'missed round' isn't a 'missed company'.

DFJ Growth passed on a pre-revenue LinkedIn at a $1B valuation because they lacked a clear revenue signal. This highlights a common VC pitfall: over-indexing on current financial metrics and under-valuing powerful network effects and analogous, proven business models from other tech giants.

A smaller fund size enables investments in seemingly niche but potentially lucrative sectors, such as software for dental labs. A larger fund would have to pass on such a deal, not because the founder is weak, but because the potential exit isn't large enough to satisfy their fund return model.

Initial go-to-market efforts selling directly to small businesses failed because the buyers weren't technical. After five consecutive calls revealed that SMBs outsource their IT, founder Kyle Hanslovan realized he needed to sell to Managed Service Providers (MSPs) instead of the end-users.

The most critical decision in venture isn't the final investment vote but the mid-funnel choice of which companies get a deep look. The costliest errors are false negatives—great companies dismissed prematurely. Firms should therefore optimize process hygiene at this stage, implementing mandatory post-meeting debriefs to avoid these misses.

The founders of Free Soul endured multiple rejections, including literally being laughed out of rooms. They frame this brutal process as a necessary filter that weeded out misaligned VCs and ultimately led them to investors who were personally connected to their mission.