I’m Jenson Cripps. I went from botting sneakers to leading AI at Fifth Wall.

I’m the AI Lead at Fifth Wall and live in Santa Monica, CA. I’m interested in brutalist design, urban planning, housing affordability and machine learning.

How I got here

Sneakers

Building communities, botting, reselling and proxies

Online sneaker communities, resale and selling proxies.

2016–17

Crypto and NFTs

Investing and trading

Crypto investing from 2019, then NFTs in 2020–21.

2019–21

Cripps LLC

Real estate investing

Short-term rentals in Indianapolis. Superhost.

2021–now

Mitsui Fudosan America

Acquisitions Intern

Helped model $1B+ in multifamily, underwrite $100M+ in industrial.

2023

Homebound

Investment Strategy & Acquisitions Analyst

Acquisitions in Houston, South Florida and Dallas.

2024

Fifth Wall

AI Lead

A venture firm focused on real estate and climate technology.

2025–now

GitHub contributions

2,678 contributions in the last year, across two accounts

Projects

Portfolio Operations Automation PlatformThe case study behind Portfolio OS: LLM document parsing, KPIs and instant memos.2025LangGraph Underwriting AgentFlood zone, deed restriction and lot checks for infill single-family deals.NowSFH Underwriting & Visualization PlatformA web app for single-family construction decisions.NowAVM Automation Chrome ExtensionRedfin estimates, injected into the underwriting application.Now
Spatial Walkability and Home Prices ModelHome values against walkability, across major metros.2024
Short-Term Rental Data ToolScraping and analysis for my own investing.2021

Fun projects