Douglas Watson
Play Money · Portfolio
Est. 2026

Douglas Watson

3 investments · 2 sectors · 1 with a why · first check 2026
No. 01 · Where to start
2026

Cache AI

Powering data-driven insights for athletes, teams and brands

Why Douglas wrote the check
Measured Capital invested in Cache AI because of the founder. I met Kobi at a startup event and was drawn to her immediately, along with the caliber of team she's assembled. She's a two-time founder with a successful exit behind her. She knows what it takes to build, and her team is positioned to execute on the infrastructure layer for NIL. They've already secured access to some of the largest colleges and universities in the country, and that momentum shows no signs of slowing.

The portfolio

2 more · 1 in Douglas' words
No. 02Accelerate Wind
WIND ENERGY · 2026

Unlocking onsite wind energy with an affordable wind turbine for commercial buildings

No. 03Cyphr AI
FINTECH · 2026

Making today's small business legible to yesterday's capital system