The Power of Acquisition: Building a Multi-Site Healthcare Platform w/ Alan Kaplan

Episode notes

What happens when a surgeon trades the operating room for the boardroom—and buys three companies in 10 days? In this episode, Alan Pentz speaks with Alan Kaplan, Co-Founder & Chief Medical Officer of Alleviate Care, about his journey from practicing medicine to building a healthcare platform through entrepreneurship by acquisition. Kaplan shares candid stories—from acquiring three hospice businesses in 10 days, to turning regulation into a competitive moat, to differentiating in a “commodity” market with storytelling and brand. He also explains how his team balances debt, compliance, and growth without VC funding, while experimenting with both acquisitions and organic expansion. This conversation is packed with insights for professional service firm owners in the $1–4M range who are exploring acquisitions, operating in regulated markets, or looking for ways to stand out when everyone seems to offer the same thing. You’ll learn: Why regulation can be an advantage, not just a barrier How to grow in slow-moving industries with acquisitions and brand strategy The power of basic competence and credibility in building trust Lessons on scaling services businesses with limited capital