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.

In this episode of The Backchannel, I’m sharing some thoughts on goals for the year—what I’m focusing on, what’s working so far, and what still needs improvement. From business to personal challenges, I’m experimenting with new approaches and seeing where they lead. If you’ve set goals for yourself, I’d love to hear them. Let’s keep each other accountable!

How do you convince investors to back you when your company’s growth has been stagnant? In this episode, we explore a question from a founder about breaking through that barrier. We’ll dive into what investors are really looking for, the importance of showing a shift or inflection point in your business, and how to craft a compelling story about the future. Plus, some thoughts on when it’s time to step back and rethink your approach before seeking investment.

In this episode of The Backchannel, Jason reflects on his own fundraising experience and breaks down the layers of what it really takes to secure investor commitments. Using his 2017 fundraise as a backdrop, he shares insights on the role of connections, the limits of those advantages, and why getting your foot in the door is just the beginning. Whether you're a founder navigating the challenges of raising capital or just curious about the process, this episode offers a candid look at the dynamics of building relationships, crafting a compelling story, and making your pitch count.

This episode of The Backchannel breaks down how the expectations for early-stage founders have shifted in the AI era. Inspired by a conversation with Jeff Bussgang—Harvard Business School professor and author of The Experimentation Machine—we explore what venture capitalists are looking for before investing. From validating your idea to leveraging AI and affordable global talent, the bar for getting to product-market fit is higher than ever. If you're building a startup or gearing up to raise funding, this episode lays out what it takes to stand out.

In this New Year’s episode of The Back Channel, we talk about the power of simple outreach and why reconnecting with your network can be the best business development move for the year ahead. Drawing from personal stories and founder advice, we explore the impact of small, thoughtful gestures—like a quick “Happy New Year” note—and how they open doors for future opportunities, from fundraising to partnerships. Whether you're looking to raise capital or strengthen connections, this episode covers practical tips to kickstart your year with intention and momentum.

In this episode of The Backchannel, we ask a critical question for founders: Should you actually be raising venture capital?

We break down why most founders chasing VC money are doing it for the wrong reasons—whether it's validation, peer pressure, or simply not knowing other options. We also explore two common categories of founders who mistakenly pursue VC dollars and share practical ways to rethink your funding strategy.

If you’ve ever considered raising venture capital, this episode will challenge you to reflect on your motivations and explore smarter, more sustainable ways to build and grow your business.