Jeff (J.D.) Davids

Why Raising Venture Capital Feels Like Going on First Dates... I just got off a meeting hosted by Fidelity Private Shares and Metal and moderated by Kristen Craft and Adam Roberts. It was an incredible discussion about the transition from pre-seed to seed, what investors are actually looking for, and the realities founders face during the fundraising process. But while listening to the conversation, something hit me that I’ve been noticing for a while now. Raising venture capital feels a lot like dating. And the parallels are kind of hilarious. When you pitch a VC, it’s essentially a first date. You want to highlight the positives. You want to show confidence. You want to be optimistic about the future. But if you come across too eager, too polished, or too desperate, it’s a turnoff. Sound familiar? On the flip side, if you’re too pessimistic or overshare all the risks too early, you can scare people away before they’ve had a chance to see the bigger vision. Dating advice and fundraising advice suddenly start sounding identical: • Be confident, but not arrogant • Be honest, but not overly self-deprecating • Show ambition, but don’t oversell Then there’s the follow-up game. After a pitch, maybe the VC doesn’t respond immediately. So the founder asks the same question someone asks after a first date: How long do I wait before following up? One day? Three days? A week? And just like dating, double-texting energy is real. Send too many follow-ups with no substance and suddenly you’re the founder version of: “Hey… just checking in 🙂” Which is rarely a good look. The funniest parallel came when the VCs talked about turning founders down. Often they really like the team. They like the vision. But the market isn’t big enough or the timing isn’t right. And instead of giving a clean “no,” founders sometimes hear things like: “We love what you’re building, but the timing isn’t right for us.” or “We just don’t have the capital allocated for this right now.” One of the speakers said something that stuck with me: If a VC really wants to invest, they’ll find a way. Which again sounds exactly like dating advice. When someone is truly interested, the signal is clear. They make time. They follow up. They lean in. When they’re not, the responses start sounding suspiciously like a polite breakup. At the end of the day, fundraising really is a two-way relationship. Founders are looking for partners who believe in the vision. Investors are looking for founders they trust to execute. And just like dating, the goal isn’t to convince everyone. It’s to find the right match. Huge thanks again to Haley Bryant of Hustle Fund and Renny M. of First In for sharing their insights during today’s discussion, it was incredibly valuable. For any founders out there raising right now… Stay confident, keep building, and remember: Sometimes fundraising isn’t about pitching better. It’s just about finding the investor who’s actually ready to say yes. --Lucas

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