Ryan Hollingshead

about

I'm currently working in SF at a Series A fintech startup called Two Dots. We're automating the income verification process for rental applications. I wear tons of different hats in my bizops role, from recruiting to tracking customer retention and contraction.

Before this, I graduated from Stanford, where I concentrated on International Relations and Data Science within the Political Science major. I also was lucky enough to take some GSB courses focused on startups, negotiations, and sports business. Some additional past experiences:

• Healthcare consulting @ Mindfrog
• Venture capital @ Correlation Ventures
• ML internship @ Dynam.AI

projects

I've recently built a team ratings page for every college football team. It has a power rating model, a resume rating model, and a breakdown for how first-year head coaches are faring so far.

I also built an interactive tool that projects every Premier League player's impact on their team's projected points. And, I put together full team projections for the season.

writing

In addition to startups and investing, I think a lot about sports, especially football and soccer. I share my thoughts on my Substack. A few pieces from there:

• Clearing out the notebook (October 2026)
• West Ham’s relegation - and what we can learn from it (May 2026)
• Sometimes, the Human Element Cannot be Replaced (November 2025)
• David Protein: Diving Deeper (August 2025)

in addition

I'm an avid golfer. My favorite course as of now is Te Arai South in New Zealand.

I've also gotten more interested in hiking recently. The Presidio is a great local option. Also had a great time at the Jenner Headlands Preserve.

I'm also a Chargers and Tottenham fan. Very confident that Tottenham will turn things around! Wish I could say the same about the Chargers.