In this episode of The Drafting Table, Jess sits down with her teammate, Work-Bench investor Daniel Chesley for a rare behind-the-scenes look at how early-stage VC decisions actually get made.
If you’re a pre-seed or seed-stage founder, this is the real talk you’ve been craving—but rarely get from investors.
We break down:
- What separates a great wedge from a forgettable one
- Why your “champagne problem” might not be a real market
- How to package your pitch to stand out in a saturated category
- The #1 data room mistake most founders make
- Why storytelling isn’t optional (even if you’re technical)
- The true test of grit we look for in early-stage teams
- And how the best founders accelerate learning through fast experiments
Plus: Our favorite tactics for breaking into legacy markets, why “thesis-driven VC” is mostly BS, and the one thing every founder should include in their intro blurbs.
Whether you’re about to raise or just sketching out your first idea—this one’s packed with tactical gems.
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