In the world of investments, everyone talks about deal flow, due diligence, and cap tables. But after two decades of building one of the most active angel investment communities in the Pacific Northwest, Nathan McDonald learned something that doesn’t show up in any pitch deck: the real value isn’t in the first meeting. It’s in the third conversation.

It sounds simple. But it changes everything about how you approach community, relationships, and ultimately, how you build and fund great companies.

The First Conversation Is Just the Beginning

Think about the last time you met someone at an investor event. You exchanged backgrounds, talked about what you’re working on, and maybe connected on LinkedIn. It was pleasant. Useful, even. But did anything transformative come out of it? Probably not — and that’s okay.

The first conversation is about orientation. You’re figuring out who someone is, what they care about, and whether there’s a reason to keep talking. The second conversation goes a little deeper — you start to see where your interests overlap, where there might be a fit.

But the third? That’s where the walls come down. That’s where a founder stops pitching and starts problem-solving out loud. That’s where an investor stops evaluating and starts advising. That’s where something real begins.

Transactions Are Easy. Relationships Are Rare.

The venture ecosystem has long optimized for speed — fast pitches, quick decisions, efficient capital deployment. And there’s a place for all of that. But what we’ve consistently seen, across hundreds of companies and thousands of investor interactions, is that the best outcomes rarely come from the fastest transactions.

They come from investors who stuck around long enough to truly understand a founder’s vision. From mentors who showed up not just at the pitch, but at the pivot. From relationships that were built slowly, over multiple touchpoints, and deepened through shared experience.

When Nathan McDonald reflected on Ecosystem Venture Group’s journey at the Investor Capital Expo, he put it plainly: “The value is not transactions — it’s created and concentrated in the conversations, the discussions, the relationships.”

That’s not just a philosophy. It’s a pattern we’ve watched play out again and again.

Why Most Networking Doesn’t Work — And What Does

Most networking events are designed for first conversations. You show up, you circulate, you collect cards or contacts, and you leave. Maybe you follow up, maybe you don’t. The format itself works against depth.

What actually works is repeated, intentional proximity — putting the right people in the same room, more than once, over time, with a shared purpose holding them together. It’s why long-standing investment communities consistently outperform one-off pitch competitions. It’s why the investors who add the most value aren’t always the ones who wrote the biggest checks — they’re the ones who kept showing up.

The magic isn’t in the event. It’s in what happens between the events, and after them, and in the quiet conversations that stretch well past the scheduled agenda.

Building for the Long Conversation

So what does this mean in practice — for investors and founders?

For investors, it means resisting the urge to evaluate and move on. Stay curious about the founders you meet, even when the timing isn’t right. The company that isn’t ready today might be exactly the right opportunity eighteen months from now — and you’ll be the first call because you never stopped paying attention.

For founders, it means investing in relationships before you need them. The investors and advisors who will show up for you in the hard moments are rarely the ones you met last week. They’re the ones you’ve been building trust with quietly, over time.

In investing, we talk a lot about compounding returns. But the most powerful compounding we’ve witnessed isn’t financial — it’s relational. Every meaningful conversation builds on the last. Every deepened relationship opens new doors. Every third conversation makes the fourth one richer.

At Ecosystem Venture Group, this is what we’re building toward: not just a network of investors and founders, but a living community where relationships are given the time and space to become something real. Where the third conversation is just the beginning.

Because that’s where the best things happen.