This article is about something I’ll refer to as the “Catastrophic Arbitrage” strategy for startup health insurance. Last year, through Venteur’s employee health benefits, I bought an Eight Sleep Pod mattress. I paid for a full year of gym membership. I covered my Whoop and its annual subscription. Therapy sessions, prescription drugs, all of it. Tax-free, reimbursed by my employer, fully legal. Today, I run a six-person startup based in NYC and SF. And the strategy I used is available to basically any young team with employees in New York City. Most just don't know about it.
