How Gary Vee makes millions beyond ads and sponsorships

Executive overview

Most influencers monetize with ads, courses, and merch. Gary Vee built real businesses instead, using his audience as a distribution asset rather than a revenue line.

The core insight: attention is a multiplier — point it at big businesses, not small ones.

Gary's side hustles and their returns

1. Empathy Wines — direct-to-consumer wine brand co-founded in 2019, cutting distributors to sell straight to buyers. Sold 15,000+ cases at ~$60/case and had 2,000 subscribers on a quarterly box at $51. Generated ~$1.3M in year one. Sold to Constellation ~12 months later for an estimated $3–6M.
2. Speaking gigs — commands $75K–$100K per event. Did ~60 events in 2019 for an estimated $6M/year.
3. Book deals — four NYT bestsellers, ~850,000 books sold, estimated $2.5M total at $3/book.
4. Television — appeared on Apple's Planet of the Apps (2017). Show was cancelled after 10 episodes; estimated $50K/episode for a ~$500K payday.
5. Angel investing — early investor in Twitter, Tumblr, Uber, and Snapchat. All became multi-billion-dollar companies.

The model worth copying

• Build audience first, then direct it at high-value businesses — not micro-monetisation.
• Free content raises brand value, which compounds across speaking, books, and deals.
• Selling a brand early (Empathy Wines) can return a fast multiple on revenue.