Funded | How They Raised Millions

TBC 148: How Simple Is Too Simple for Your Pitch Narrative

Founders almost never cut their narrative far enough. In this episode of The Backchannel, Jason shares a lesson from one of the best negotiators he’s ever seen — push all the way to the line so you know where it is. Applied to pitch narratives, that means going so simple it feels dumb, and then layering complexity back in from there. If you’ve been gradually trimming your story and wondering if you’ve cut enough, this episode will change how you approach it.

TBC 147: Your Numbers Are Part of the Story, Not Separate From It

A lot of founders treat storytelling and hard data as two different things in a pitch — and that’s the mistake. In this episode of The Backchannel, Jason breaks down why your numbers mean nothing without a narrative wrapped around them, and why letting investors interpret raw data on their own is one of the most common pitching errors he sees. If you’ve ever wondered how much to lean on story vs. facts, this episode reframes the question entirely.

TBC 146: Why VCs Only Remember the Last Thing They Heard

Venture capitalists don't have a perfectly indexed CRM in their heads. They run on recency bias — last in, first out. In this episode of The Backchannel, Jason breaks down what he realized after bumping into a top VC at a cafe in San Francisco: investors share what’s freshest in their minds, not what’s most relevant. He explains what that means for how founders should think about messaging, surface area, and staying top of mind — without being manipulative about it.

TBC 145: Stop Blending Your Ask Into Your Personal Emails

Most founders make the same mistake when reaching out to their network during a fundraise, they try to combine a personal connection with a business ask in the same email, and end up doing both badly. In this episode of The Backchannel, Jason breaks down why blended emails feel disingenuous, and introduces his email appendix format: a simple structural shift that separates the personal from the functional so both actually land. If you’ve ever sent an awkward “hey, how’s your summer going, by the way I need a favor” email, this one’s for you.

TBC 144: Why You Don't Need Money to Start Moving

Too many founders think they need capital before they can make real progress — but that's exactly the mindset that keeps them stuck. In this episode, Jason breaks down the "parked car" trap: why waiting for funding before moving forward is the wrong approach, and how to start building momentum now so investors see a moving train, not a standstill. If you're preparing to raise your first round, this one's for you.