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.

In this episode of The Backchannel, we break down the concept of closing dates in fundraising and why they’re a powerful psychological tool rather than a legal requirement. Learn how closing dates create urgency, push investors to commit, and help fundraisers organize their rounds effectively. Whether you're a startup founder or a fund manager, this episode will help you understand how to set and communicate closing dates to drive decisions and close your round with confidence.

In this episode of The Backchannel, we dive into the trade-offs between maximizing valuation and keeping deal terms simple. Whether you're a founder chasing a higher valuation or an investor protecting optics, adding deal structure can have long-term implications. Learn why simplicity often wins in the end and how complex terms like liquidation preferences, warrants, and dilution protections can create friction for future rounds. Tune in to hear why aiming for a clean deal benefits everyone in the long run.

In this episode of The Backchannel, we explore how to prepare for final VC meetings, what investors are really looking for, and how to handle the pressure of tough questions. Whether you're a first-time founder or a seasoned entrepreneur, this episode is packed with actionable insights to help you close the deal with confidence.

In this episode of The Backchannel, we explore strategies to help a founder turn investor interest into momentum during a challenging fundraise. From avoiding reliance on a single viral moment to showcasing consistent progress, we discuss practical ways to create the perception of unstoppable growth. Whether you’re pitching now or planning your next round, this episode offers sharp, actionable insights for closing strong.

In this episode of The Backchannel, we talk about the realities of raising capital and why many founders may not be ready for venture funding. Instead, we explore the often-overlooked world of angel investing—who angel investors are, how to find them, and how to tailor your pitch to different types of angels. Whether you’re building a billion-dollar startup or a sustainable small business, this episode offers a practical playbook on how to secure early-stage funding.

In this episode of The Backchannel, Jason unpacks why many founders struggle to raise capital in today’s cautious VC environment and offers alternative strategies to keep momentum. Learn how to tap into angel investors, leverage AI, and access global talent to build traction on a lean budget. Tune in to hear how you can turn obstacles into opportunities—and don’t miss the next episode, where Jason breaks down the art of pitching to angel investors.

In this episode of The Backchannel, we explore why making in-person connections can be a game-changer for founders. Recorded on location in Austin, Texas, Jason shares insights sparked by his own travel experiences, focusing on why meeting face-to-face can have a major impact on relationship-building, especially when it comes to securing investments.

In this episode of The Backchannel, we're dropping a quick but essential take on balancing brilliance and likability and how both play into the fundraising game. We revisit a core concept from a past episode: time given – time to interest. If your brilliance gets investors hooked fast, you don’t need as much relationship-building. But if it takes longer to spark that interest, likability becomes your best tool for buying more time. We also talk about how being difficult, even if you’re brilliant, can close doors.

‍