Episode stack: https://stackl.ist/4baJeZm

We taught computers to do math, then to write. Jared White thinks the real unlock is teaching them to read, and he's proving it in the one place that punishes a wrong answer hardest: the courtroom.

Kyle sits down with Jared, founder and CEO of Matey AI, whose path runs from building quantitative trading desks in Austin, through a stint in crypto, to an AI-native legal company built for criminal defense.

They get into why he started in the least forgiving domain he could find, how the economics of building have flipped, and the advice he'd give a younger founder: start with the customer, because implementation is the easy part now.

In this episode:

0:00 Intro — coffee mugs, merch, and a Matey logo story
5:35 Pricing as a moving target (version 18 and counting)
7:33 Reading a Cursor bill as an asset, not an expense
10:26 Jared's path: software, burnout, and building a trading desk
17:25 Naming Matey: the Wordle of the day and "your first mate"
20:22 Why this feels like the early web all over again
24:34 When AI coding finally got good enough to trust
28:17 Why start in legal — the least forgiving problem
30:55 "Executive Mate": an AI that could run a company
31:49 Scaling the team, hiring misfires, and the data problem
37:37 Human-in-the-loop, shrinking toward zero
40:38 The raise, and a go-to-market year ahead
50:19 Advice to a younger founder: start with the customer