About
A practitioner buying and running one company.
The firm
Tail Risk is my company to acquire and grow a single cybersecurity, risk or compliance business, and to lead it myself for the long term.
Across my career in technology risk I've been a practitioner, an entrepreneur, a consultant and an investor. Tail Risk brings those together in one place: a search for a single company that I will buy and run, not flip.
We believe in hard work, creative problem solving and leading by example.
About Rob
Most recently I was Chief Information Security Officer at Synechron, a global IT services firm. From 2022 to 2024 I was VP of Digital at Energy Impact Partners, an investment firm backed by more than 65 industrials and utilities. Before that I led M&A for Deloitte's U.S. Cyber practice, where we acquired six businesses in two years. After business school I co-founded and led a cybersecurity services firm, and I began my career in cybersecurity consulting.
I hold a B.A. in Economics and Russian Studies from Washington & Lee University and an MBA/MIA from Columbia University.
My wife, daughter, dog and I live in New York, and we're open to relocating for the right company. I was captain of my college wrestling team, I'm a Brazilian jiu-jitsu purple belt, and outside of work I spend my time on reading, skiing, travel and board games.
Backed by
Institutional investors and experienced operators.
Committed capital from firms and individuals who have built, bought and led technology businesses. They back the search; I make the decisions.
- Alfonso Blohm
- Michael Horowitz
- Diego Cuenca
- John Edwards
- Sonny Sinha
- David Farahi