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

Homebound

Investment Strategy

Brought machine learning into underwriting to open new markets.

2024

Fifth Wall

AI Lead

A venture firm focused on real estate and climate technology.

2025–now

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

GitHub contributions

2,684 contributions in the last year, across two accounts

Highlighted Coursework

Generative AI in the WildHow generative models are reshaping creative work, the economy and the law.2023
Auditing AIAuditing models for fairness and risk through labs and case studies.2023
Unstructured Data AnalyticsText and other messy data, up to neural networks.2023
Simulation and OptimizationModeling uncertainty and finding the best decision under it.2023
Machine LearningBuilding, evaluating and improving predictive models.2024
Urban AnalyticsSpatial data, text mining, deep learning and LLMs applied to cities.2024

Fun projects