Jess Richmond thinks the premium on technical founders is about to flip. Building is cheap enough now that anyone can ship a bookkeeping app in a week. What's scarce, she argues, is having actually lived the problem: reconciled the transaction, sat in the procurement meeting, knows exactly what a customer will and won't trust.

She pitched Blackbird on Sumday with a screenshotted SharePoint site. Four years on, she's betting the company on government agencies, the buyers with the least patience for anyone who hasn't already done the work of understanding how they operate.

Kate sits down with Jess to talk about why not knowing venture capital's unwritten rules might have made her braver rather than naive, the $50,000 supplier decision that never accounted for its own emissions, and how she reverse-engineers a buyer's psychology before she ever mentions the product.