The Trust You Build Between Meetings: My Conversation with Kevin Bennett
Dividends are small. Nobody gets excited about a quarterly payout the size of a cup of coffee. But they accumulate, and soon, they can outgrow the original investment entirely.
In the latest episode of Raiser’s Edge, Kevin Bennett, who has raised over $200M for his companies HomeZen, Caribou, and now Further, borrows this idea to describe how building a relationship with investors actually works. For Kevin, it’s about small, often seemingly unremarkable deposits — showing up on time, doing what you said you’d do, telling someone something true before they ask — that accumulate to build the confidence an investor needs to fund something that doesn’t sell itself on the numbers alone. He calls it the “trust dividend”, and it’s a big part of how he’s been able to achieve success in often unfavorable categories, including achieving unicorn status for his company Caribou.
Here are some of my takeaways from my conversation with Kevin.
1. Admitting what you don’t know is actually a sign of strength.
I asked Kevin how he learned to fundraise. His answer started where you’d expect — learn by doing, more of what works, less of what doesn’t — but the real insight was one level down: the most important skill isn’t any individual fundraising tactic, it’s “learning how to learn.” Being perceptive enough to notice what’s actually resonating, and asking the right questions to find out.
The specific move he named is almost embarrassingly simple: when you don’t know something, say so. Founders, especially insecure ones, default to performing certainty and acting like they have an answer for everything. Kevin’s read is that this backfires. Transparency about your own thinking, including the gaps in it, is what actually builds investor confidence, because it signals you’re giving them the full story instead of a curated one. The dividend isn’t paid by looking like you have it all figured out. It’s paid by being honest about the parts you don’t.
2. Find the right dance partner.
Kevin told me about pitching a high-profile investor years ago. A few good conversations, even dinner out in the Valley to talk through the business. Then it just stopped without a real explanation. Weeks later, the feedback came back through a different investor: the guy had spent the whole night needling him, hoping to provoke him into wanting to throw a punch. Kevin never took the bait. That, somehow, was the problem.
Kevin’s take on it: that investor was looking for a fight club conversation, Kevin was looking for a trust dividend conversation. Two completely different ways of building a relationship — neither one wrong on its own, but if you’re not the same kind of investor or founder, no amount of chemistry closes that gap. Early in his career, he said, this kind of pass from an investor made no sense to him; he assumed it reflected on his business. In hindsight, it had nothing to do with the business and everything to do with fit. He didn’t lose that investor. He found out, for free, that they were never going to be the right partner anyway.
3. Learn how they weather the storm.
Kevin has a go-to question when he’s getting to know someone: what’s the hardest thing you’ve ever done, personally or professionally? He says people take about half a second to decide whether they trust you — and if they do, the answer is almost always personal, because the hardest thing anyone’s done usually is.
What he’s actually listening for isn’t the story itself. It’s the narrative structure underneath it. Kevin hopes to hear an answer that sounds less about and, in his words, more like “this happened, and here’s what I did about it, and here’s what I learned.” Agency, not just hardship. Startups are hard in a specific, recurring way, and Kevin’s bet is that people who’ve already metabolized one hard thing into a story about their own agency are the ones who’ll be good at the next one. It’s a qualifying question and a trust-building one at the same time — the asking is itself a small risk, and the answering is a bigger one, and both sides walk away knowing more than they did sixty seconds earlier.
Kevin’s closing advice to founders was to be 100% the best version of yourself — not 98%, not 99%. It’s the kind of line that could risk sounding like an inspirational poster if Kevin wasn’t such an exemplar of putting that advice into action. Everything in the conversation is really just a description of what that looks like in practice: relationship over transaction, honesty over performed certainty, every touch point treated as real instead of incidental.
None of it is a cheat code, or a secret hack. That might be the point. The dividend doesn’t pay out because you found the trick. It pays out because you kept making the deposit when it would have been easier not to.
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Stay sharp,
Ben