Keeping It Real In Your Raise: My Conversation with Evan Kaplan
On playing your cards not only right, but honestly.
Welcome back to Raiser’s Edge!
When my longtime friend & venture investor Gus Tai suggested interviewing Evan Kaplan for this podcast, it was a no-brainer.
As CEO of Aventail, iPass, and InfluxData, he’s raised over $400. But more importantly, he has survived countless market peaks and valleys—not to mention near-death experiences—with incredible resilience. Evan was one of the first people I asked for advice back when I was raising my own first rounds, and he’s coached so many other founders through their own tough fundraising situations.
Here are some of the key insights I took away from my conversation with Evan, that every entrepreneur can learn from:
1. Know how your investor gets paid.
Most founders never learn the nuts and bolts of venture capital mechanics. Evan emphasized just how important it is to learn what’s happening behind the scenes for your potential investor—not just what they care about, but literally the structure and economics behind their fund. Where are they in their fund lifecycle? What returns do you need to hit to be “worth their attention”? What do they need to prove to their LP’s to raise their own next fund? If you want to get them on your cap table, get curious and ask them about their own business—how they think, what excites them, and how they structure their day-to-day decisions.
Most entrepreneurs wouldn’t even think of extending that kind of empathy to an investor. But Evan shows how it leads to a much better understanding of the investor and what makes them tick—and gives you intel to gain a capital advantage.
2. Action speaks louder than words.
There are dozens of moments when the ball is in the investor’s court in the lead up to a venture round, and any one of them can be a show-stopper. Evan tracks who delivers and who delays on these steps, separating out the investors who are truly committed to their partnership from the ones who will inevitably become roadblocks for the company. In a world filled with gratuitous happy talk and unexplained ghosting, Evan uses follow-through as his signal to forecast honest partnership and future success.
3. Building a relationship isn’t optional—it’s the whole point.
Early in our conversation, I asked Evan whether fundraising is a relationship or a transaction, and his response was quick and unwavering: “Has to be a relationship.” Fundraising is much more than securing capital—it’s laying the groundwork for your company’s future partnerships, board dynamics, and strategies. The investors you bring on will be in the trenches with you, and how you build that early relationship sets the tone for years (and sometimes entire company lifecycles) ahead.
Evan’s lessons are battle-tested, and he has the receipts – and the scars – to prove them. For anyone in the thick of it, feeling run down by the process, he reminds us that at the end of the day, the best thing you can do is also the simplest thing: Drop the bravado and show up with your full self.
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Stay sharp,
Ben