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If it's not a Hell Yes!!!, it's a No

In my experience, discerning an investor's commitment to funding my business has been relatively straightforward after the initial meeting. While there have been instances of initial enthusiasm not translating into investment, I've never encountered the reverse scenario. I consider this a reliable observation, and here's why:

Although a venture capital (VC) firm's fund is what ultimately appears on their portfolio, it's typically a specific partner who spearheads the internal decision-making process. Assuming the role of deal leader suggests that this partner is thoroughly convinced of your company's potential to be a standout investment. This conviction is often formed, or at least strongly hinted at, during the initial meeting. While subsequent discussions may temper the investor's initial excitement for various reasons, I've yet to witness a case where an investor started lukewarm and then became enthusiastic after multiple meetings. So, if an investor is not enthusiastic to start, they’re not going to invest.

To illustrate the numerical challenge of standing out amongst your peer companies to investors, consider this example: 

A VC firm with three partners collectively invests in 12 new companies annually, translating to an average of one new investment per quarter per partner. Now, suppose each partner evaluates 25 companies per week, totaling 100 companies per month or 300 companies per quarter. For your company to be "The One," it must rank number one out of these 300 contenders—not number three or seven, but the top choice. Given this competitive landscape, it's reasonable to assume that if an investor identifies your company as potentially The One, they'll communicate this enthusiasm clearly and decisively. Even if they include your company in their top 30 (10 per month) for further consideration and diligence, you should be able to discern your elevated status as part of their elite investment opportunities after just one meeting. While you may not end up securing their investment (resulting in a false positive), you'll know you're among their top opportunities. Conversely, if your company ranks 40th, it's unlikely that anything in your current fundraising efforts will propel you to the top of their list (which is not to say that revisiting the investor in a subsequent fundraising round could not lead to a different outcome).

To wrap up, the "Hell Yes!!!" principle serves as a practical guideline in gauging investor interest. If the initial response falls short of enthusiastic affirmation, it's often indicative of a less favorable outcome in the funding journey.