$50k → $5M buying declining healthcare businesses (here's how) | Devin Fitzgerald episode artwork

EPISODE · Nov 7, 2025 · 51 MIN

$50k → $5M buying declining healthcare businesses (here's how) | Devin Fitzgerald

from The SMB Deal Hunter Podcast · host Helen Guo

Devin Fitzgerald acquired 2 declining home healthcare businesses in the Boston area over the last few years and successfully turned them around. He did it with some of the most creative financing we’ve seen on the show. And he’s already working on acquisition #3 (which is 4x bigger than all of his current businesses combined). At some points his story is nearly unbelievable. Here are just a few snippets from his interview...🔥 He bought his first two healthcare businesses making ~$5M in Revenue with only $50k down (and says he shouldn't have put down anything at all)🔥 He was negotiating six-figure deals while delivering pizzas—literally putting bankers on hold to hand off a pepperoni pizza for a $3 tip🔥 He bought a business declining 21.5% per year with zero healthcare experience (and turned it around in year one). Then did it again with business #2 (declining ~6% a year).And some of his insightful lessons: ❓ Why he bought declining businesses (one falling 21.5% annually) when most buyers would run away❓ The book that completely changed his integration strategy (hint: it's about Warren Buffett and John Malone)❓ How he's differentiating in healthcare where rates are often capped and everyone competes on the same playing field-------------------------------👉 Subscribe to the SMB Deal Hunter Newsletter — free weekly deals & insights: https://join.smbdealhunter.xyz🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz💼 Connect with me on LinkedIn: https://www.linkedin.com/in/helen-guo-06674523/

Devin Fitzgerald acquired 2 declining home healthcare businesses in the Boston area over the last few years and successfully turned them around. He did it with some of the most creative financing we’ve seen on the show. And he’s already working on acquisition #3 (which is 4x bigger than all of his current businesses combined). At some points his story is nearly unbelievable. Here are just a few snippets from his interview...🔥 He bought his first two healthcare businesses making ~$5M in Revenue with only $50k down (and says he shouldn't have put down anything at all)🔥 He was negotiating six-figure deals while delivering pizzas—literally putting bankers on hold to hand off a pepperoni pizza for a $3 tip🔥 He bought a business declining 21.5% per year with zero healthcare experience (and turned it around in year one). Then did it again with business #2 (declining ~6% a year).And some of his insightful lessons: ❓ Why he bought declining businesses (one falling 21.5% annually) when most buyers would run away❓ The book that completely changed his integration strategy (hint: it's about Warren Buffett and John Malone)❓ How he's differentiating in healthcare where rates are often capped and everyone competes on the same playing field-------------------------------👉 Subscribe to the SMB Deal Hunter Newsletter — free weekly deals & insights: https://join.smbdealhunter.xyz🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz💼 Connect with me on LinkedIn: https://www.linkedin.com/in/helen-guo-06674523/

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$50k → $5M buying declining healthcare businesses (here's how) | Devin Fitzgerald

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This episode was published on November 7, 2025.

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Devin Fitzgerald acquired 2 declining home healthcare businesses in the Boston area over the last few years and successfully turned them around. He did it with some of the most creative financing we’ve seen on the show. And he’s already working on...

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