In this episode of Founder2Founder, Aaron Spivak sits down with Heath Wolfson, serial entrepreneur and founder of FrontCare, a creator-powered telehealth platform. With a 20-year track record of building businesses across safety, media, and health, Heath shares how he’s repeatedly turned market inefficiencies into high-growth ventures.

He opens up about navigating failure, executing without outside capital, and spotting cultural trends before they explode. From launching Tattoo Nation in shopping malls to scaling one of Facebook’s biggest publishing engines, Heath now turns his focus to reshaping healthcare access through affiliate-driven telehealth.

Chapters:
02:49 – Early Life, College, and First Entrepreneurial Sparks
03:57 – A Practical Approach to Entrepreneurship
04:58 – The First Business: Event Marketing in NYC
06:35 – Lessons from a Short-Lived Nightlife Venture
07:51 – A Quick Detour at Morgan Stanley
08:52 – Bringing Tattoo Parlors to Shopping Malls
10:35 – Navigating Regulations in Traditional Retail
12:45 – The 2008 Crash and a Failed Expansion
13:56 – Forgetting a $100M Success: Glow-in-the-Dark Safety
15:56 – Getting a Law Passed and Building a Manufacturing Deal
17:19 – How a Nightlife Job Led to a Fortune
19:22 – Partnership, Production, and Exit to a National Brand
21:49 – Real-Time Pattern Recognition and Risk
22:32 – Understanding Market Timing and Survival
24:11 – Acquiring Inked Magazine and Going Omnichannel
25:36 – The Birth of Facebook E-Commerce
27:00 – Owning and Monetizing Massive Facebook Pages
28:38 – Cambridge Analytica Fallout and Platform Risk
30:51 – Why Timing is Everything in Business
32:22 – The Dangers of Scaling Too Fast
33:42 – Zooming Out: Lessons Over Two Decades
34:46 – Transitioning from Media to Health
35:38 – Accidentally Overdosing on Ozempic
37:48 – Experiencing the Power of GLP-1s Firsthand
39:21 – Bootstrapping a Brick-and-Mortar Weight Loss Clinic
40:51 – Selling Telehealth Models to Founders and Creators
43:11 – Breaking Down the Legal Fight Between Compounders and Big Pharma
44:36 – Making Health an Empowered Conversation for Creators
45:52 – Building a Trust-Based Health Affiliate Ecosystem
47:31 – Quality Control and Compliance in Telehealth
48:45 – Inside the FrontCare “Clinic as a Service” Model
49:46 – Helping Gyms, Salons & Clinics Monetize Wellness
50:38 – Legacy Thinking and the Next Chapter
52:26 – Advice to His 17-Year-Old Self: Buy Real Estate
53:56 – Why Money is a Tool, Not a Destination
55:07 – Empowering Through Access and Ownership

Guest Links:
LinkedIn: Heath Wolfson

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