HeyBenny

Benny is a fintech platform founded in 2023 by Matt Malenfant and Mark Cigainero that solves a narrow but real problem: many employees at public companies have access to Employee Stock Purchase Plans (ESPPs) that offer meaningful discounts (typically 15% off the stock price, with additional look-back pricing benefits), but can't afford to max out their contribution without disrupting their monthly cash flow. Benny provides a short-term advance to bridge that gap — you set aside the full 15% of your paycheck into the ESPP, Benny advances you most of that money back to cover monthly expenses, and at the end of the ESPP offering period, Benny takes a portion of your gains in exchange for the financing.

The mechanics are structured so that for the typical user, the deal is accretive: Benny charges a fee that's meaningfully less than the ESPP discount, so as long as the stock doesn't decline significantly below the look-back price during the offering period, both the employee and Benny come out ahead. The platform is available to employees at hundreds of participating publicly traded companies, including Apple, Microsoft, Google, and many mid-cap tech firms — and Benny handles the financing, timing, and tax documentation. Minimum investment is effectively $0 for the employee (you're investing pre-tax payroll contributions), and there is no upfront subscription fee.