In this episode of The Backchannel, Jason breaks down what it really means to fundraise in an AI-dominated world. If you’re not building core AI infrastructure, how should you position your startup? He explains why every founder needs an AI story—one rooted in how the tech impacts your product, operations, and long-term defensibility.

In this episode of The Backchannel, Jason reflects on a recent conversation with a robotics founder that reminded him how powerful it is to focus on what actually matters. From skipping the company name to delaying fundraising, the founder made unconventional decisions that signal discipline, clarity, and real momentum. Jason breaks down why avoiding “playing startup” and doing the unsexy work is often what sets great founders apart.

In this episode, we share a powerful lesson from a recent pitch practice session with a founder whose natural charisma backfired. While being articulate and engaging can be a superpower, it can also lead to rambling when clarity matters most. We talk about why “less is more” applies just as much to live pitches as it does to pitch decks—and how embracing silence can actually project more confidence. If you’ve ever talked yourself in circles during a meeting, this one’s for you.

In this episode we share the fundraising version of product market fit—what it feels like when a VC starts dreaming alongside you. We break down what that moment looks like, why it matters, and how to set up your pitch to create that kind of pull.

In this episode of The Back Channel, I reflect on a recent visit to Harvard Business School where I coached founders in Jeff Bussgang’s Launching Tech Ventures class. I break down one of the biggest fundraising mistakes I saw, how founders frame their problem space, and share advice on how to fix it.

In this episode, we explore how one small act of generosity can shape long-term relationships in venture capital. Jason shares a story from a recent trip back to Harvard Business School, where a simple coffee chat from a decade ago turned into a meaningful connection with a now-prominent VC. He reflects on what true network-building looks like—why helping others when it's easy can lead to unexpected returns years later.

In this episode of The Back Channel, we talk about the pressure founders feel to pitch a massive vision — and what actually makes that land with investors. VCs need to believe in billion-dollar outcomes, but that doesn’t mean you should throw out the biggest idea you can think of. Credibility, traction, and storytelling all shape how your vision is received. We also revisit the Airbnb pitch and why their big thinking worked — and how yours can too.

In this episode, we'll talk about green flags—the little things founders say or do that quietly leave a strong impression on investors. I share a story about a first-time founder at one of our events who said two things that really stood out. They weren’t flashy, but they revealed a surprising level of maturity... and they’re the kind of signals that stick.