James Win

Random observation from a founder relatively new to VC fundraising. I’ve only been through a Series A for one of my companies, and I’m preparing for a Series A for another. So I certainly don’t claim to be an expert on venture capital. But coming from a capital markets background, there’s something about the VC fundraising process that I find fascinating. In capital markets, if you want alpha, you do the homework. You research the market. You identify opportunities before others recognize them. You develop conviction, take a position, and hopefully capture the upside. The opportunity doesn’t come knocking on your door with a pitch deck asking you to invest. So why does venture capital sometimes seem to work in reverse? One of the most common pieces of fundraising advice I’ve received is that founders need to proactively reach out to VCs, build relationships, pitch their companies, and constantly follow up. Shouldn’t it be the other way around, too? I’m running two companies. I’ve completed one Series A and am preparing for another. I barely have time to fundraise, let alone chase VCs. Interestingly, the investors who impress me most are the persistent ones who do their homework, understand our business, and add value BEFORE getting an allocation. They’re often the ones who become our strongest supporters. If VCs only invest in founders who are good at fundraising, are they missing founders who are too busy building? Genuinely curious what founders and VCs think. I’m still learning this game.