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.

In this episode of The Backchannel, we break down a simple but powerful equation to help founders understand why some investor meetings turn into momentum—and others fall flat. We share a personal story that sparked the idea, then introduce the concept of Time Given (TG) minus Time to Interest (TTI) as a way to diagnose and improve your fundraising outcomes. If you're stuck wondering why some pitches connect and others don’t, this framework might give you a clearer path forward.

Is pre-seed fundraising harder than ever? In this episode of The Backchannel, we break down how expectations for early-stage startups have shifted. Investors now demand more proof—traction, paying customers, and even product builds—before writing checks. Why? A mix of AI-driven productivity, global talent access, and the lingering effects of the post-ZIRP investment climate. If you’re a founder navigating this new reality, this episode will help you understand what it takes to stand out. Learn how to adapt, leverage AI tools, and make progress without investor capital. Tune in to stay ahead of the curve.