Rick Apple: From Princeton to Nashville's SMB Growth Expert

Rick Apple of Upside Growth Partners began his career in New York in investment banking and private equity after graduating from Princeton before relocating to Nashville, where he and his wife are raising 5 children (!). After running a telecom company and working with Council Capital, Rick teamed up with Eric Stiller to invest in smaller businesses, beginning with the Beaufort Bonnet Company, a children's clothing brand that became a breakout success. That early win put Upside on the path to sustained success.

With 5 kids at home and 12 platforms closed, we asked Rick how he scales both life and business. For sourcing new platforms, half of their deals emerge from structured theses developed alongside operating partners, while the other half are "bumped into" through compounding networking.

Upside underwrites using what Rick calls the "3-5-7 framework." The deal must credibly deliver a 3x MOIC in a downside, the base should have a clear path to 5x, and upside potential of 7x+. This contrasts sharply with their more start-up-y "Upside 1.0" side track, where investing modest sums into early or near-break-even concepts require a 20x-type return potential to justify the commitment.

The post-acquisition playbook include 2-3 years of heavy lifting: installing systems, ERP platforms, KPIs, marketing tools, and upgrading management teams. Later in the investment lifecycle, their focus as independent sponsors shift from operator to board-level partner (e.g., strategy, M&A decisions, and capital allocation).