TBC 145: Stop Blending Your Ask Into Your Personal Emails

TBC 149: How to Actually Use Startup Advice You Find Online

Not all advice is created equal — and bite-sized content on Twitter or LinkedIn was never meant to be followed word for word. In this episode of The Backchannel, Jason gets candid about his own content, why his takes are always directionally accurate but never fully comprehensive, and how founders should be filtering and applying advice they find online. He also shares why leaving a kind comment for a creator you follow might matter more than you think.

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.