Brian Nichols is the co-founder of Angel Squad, a community where you’ll learn how to angel invest and get a chance to invest as little as $1k into Hustle Fund's top performing early-stage startups

Tony Hawk turned professional at 14 years old. By 16 he was considered the best vertical skateboarder in the world. By the late 1980s, the skating boom was over, prize money had evaporated, and he was reportedly living on $5 a day. Then the 1990s came. Skateboarding had its resurgence. And Hawk had spent the bad years building infrastructure that the resurgence would make valuable.

Birdhouse Skateboards

Tony Hawk co-founded Birdhouse Skateboards with partner Per Welinder in the early 1990s, during the skateboarding bust, not the boom. The timing was deliberate. When the sport recovered in the mid-1990s, Birdhouse had the team, the brand, and the production relationships already in place. By the time the resurgence hit, the company was generating millions in revenue annually. Hawk later acquired full ownership of the brand from his Blitz Distribution partnership.

Birdhouse became one of the most recognized skateboard brands globally. It sells boards, apparel, accessories, and produces multimedia content. Hawk's son Riley Hawk has ridden for the team. The brand is a direct expression of the principle Eric Bahn of Hustle Fund has articulated repeatedly: the best time to build is during the trough, not at the peak, because the infrastructure you build during slow periods has more durability than whatever you build when everyone is scrambling in.

The Video Game Franchise

The Tony Hawk's Pro Skater franchise, developed by Activision and released in 1999, was one of the most commercially successful sports video game series in history. The franchise sold over 20 million copies across its run and generated approximately $1.4 billion in total revenue. Hawk's deal included royalties and licensing, which turned his cultural moment into a sustained income stream across the entire lifecycle of the franchise.

The franchise was remastered in 2020 as Tony Hawk's Pro Skater 1+2, which became one of the highest-rated games of that year. The remaster introduced Hawk's brand and the skating subculture to a new generation of players who had not been alive for the original releases.

Angel Squad members studying licensing and IP as investment categories should look at how Hawk structured this deal. The franchise-as-income-stream model is rare for athletes, and it required him to negotiate equity in the cultural product he was helping to build rather than accepting a flat endorsement fee. That distinction between endorsement revenue and equity participation is one Angel Squad discusses constantly when evaluating early-stage founder compensation structures. Explore the community at hustlefund.vc/squad.

The Early Tech Investments

Tony Hawk investments outside skateboarding include some early bets that demonstrate real investment instinct. He was an early investor in Nest, the smart thermostat company, before Google acquired it for $3.2 billion in 2014. He backed Blue Bottle Coffee at an early stage, before Nestlé bought a majority stake for $500 million in 2017. These were not random diversifications. They were early positions in consumer-facing technology and lifestyle brands that fit the cultural sensibility he had spent decades cultivating.

His more recent investment portfolio through angel investing includes stakes in Cameo, the personalized celebrity video platform; Public, the social investing app; and Holey Grail Donuts, a Hawaiian-style malasada donut brand. His investment in DocuSign was also documented at an early stage.

Shiyan Koh of Hustle Fund has noted that the most interesting angel investors are the ones who combine cultural credibility with genuine product instinct. Hawk has both, and the early tech bets show he is paying attention to the consumer landscape beyond his own category.

The Skatepark Project

Hawk founded The Skatepark Project, formerly known as the Tony Hawk Foundation, in 2002. The nonprofit has invested over $11 million to build more than 600 skateparks in underserved communities across the US. The work addresses something the venture world tends to overlook: public infrastructure for youth activity in communities where real estate, tax bases, and political will are insufficient to fund it independently.

The philanthropic work also functions as brand equity for Hawk's commercial activities. Founders and investors who are seen as building for their community accumulate a kind of trust that makes every subsequent business relationship more durable.

Angel Squad members learn from investors who see their work as connected to something larger than returns. Hawk built that connection across his entire career. It is part of why his name still carries commercial weight more than two decades after his competitive peak.

The 2,500-plus members of Angel Squad across 50-plus countries engage with investing through that same lens: building real value, not just extracting it. Find them at hustlefund.vc/squad.