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.

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.