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.

Setting deadlines in fundraising can be a powerful tool—or a costly mistake. In this episode of The BackChannel, we break down how founders should think about creating urgency without scaring off investors. Learn why setting deadlines too early can backfire, how to structure a process that keeps investors engaged, and why a well-placed deadline can actually help VCs prioritize your deal. If you're raising money and wondering how to create momentum without turning investors away, this one's for you.

Investors love to test founders with tough questions—but what if you don’t know the answer? In this episode, we break down a real pitch meeting where a simple misunderstanding derailed the conversation. Learn how to handle tricky investor questions, when to ask for clarification, and why truly knowing your business makes all the difference.

In this episode of the Back Channel, we explore the art of storytelling and the balance between hard facts and narrative. A founder’s question sparks a conversation about when to lean on data and when to let the story take center stage. Tune in for thought-provoking insights on crafting compelling narratives without getting bogged down in numbers.

Most founders assume venture capital is the only way to fund their startup, but is it really the right path for you? In this episode of The Backchannel, we challenge the default fundraising mindset, breaking down why so many founders skip critical early steps. We'll shares insights on evaluating your real needs, exploring alternative funding options, and learning from those who’ve been in your shoes. Before you start pitching, make sure you’re not heading in the wrong direction.