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

Ryan Reynolds has said he doesn't consider himself an entrepreneur. That's either false modesty or a clue to how he actually operates. His businesses are collectively valued at approximately $14 billion according to Forbes, and his personal net worth sits around $350 million as of 2025. Two major exits, Aviation Gin selling to Diageo in 2020 for up to $610 million, and Mint Mobile being acquired by T-Mobile in 2023 for $1.35 billion, netted him somewhere north of $400 million combined. And Reynolds was the creative director of both, not a passive cap table name. That's the thing about Ryan Reynolds investments that most people miss. He doesn't just buy a stake. He becomes the company's unfair advantage.

Aviation Gin: The Proof of Concept

Reynolds acquired a minority stake in Aviation Gin in 2018 after trying the product and genuinely loving it. What happened next is a case study in what happens when a founder-operator type joins a small brand. He took over creative direction and started making ads that were self-aware, funny, and impossible to scroll past. Revenue grew dramatically. The brand punched far above its weight. Diageo noticed and paid up to $610 million for it in August 2020, with Reynolds estimated to have held around a 20% stake.

The Aviation Gin playbook established a template: find a brand you actually believe in, take an active creative role rather than a passive financial one, build genuine consumer affinity through honest storytelling, and let a strategic acquirer come to you. That's not the typical angel investor move. But it worked.

Mint Mobile: 50,000% Revenue Growth

Reynolds picked up a 25% stake in Mint Mobile in 2019 after connecting with the founder through a Parkinson's disease research foundation. At the time, Mint was a small prepaid wireless brand with limited brand recognition. Reynolds did what he does: became the face of the company, made commercials that people actually watched on purpose, and drove revenue growth of nearly 50,000% over three years. T-Mobile acquired Mint Mobile in a deal valued at $1.35 billion, with the FCC approving it in April 2024. Reynolds cleared an estimated $300 million on that exit.

Shiyan Koh, Hustle Fund managing partner, has talked about how brand equity is one of the most underpriced forms of competitive moat in consumer businesses. Reynolds has built his entire investment strategy around that observation, whether consciously or not.

Wrexham and the Storytelling Asset

In November 2020, Reynolds and Rob McElhenney bought Wrexham AFC, a Welsh football club sitting in the fifth tier of English soccer, for $2.5 million. That purchase spawned a Disney+ documentary, two promotions up the English football pyramid, a reported $1 billion economic boost to the Wrexham region, and a global fanbase that was essentially created from scratch. In January 2025, Reynolds and McElhenney expanded the sports portfolio by investing in La Equidad, a Colombian football club.

The Wrexham bet isn't primarily a financial calculation. It's a storytelling platform that also happens to be a business. Reynolds has always understood that a compelling narrative is a distribution channel. The Wrexham documentary has done more for Reynolds-backed brands than any traditional advertising campaign could.

The Broader Portfolio

Beyond the headline exits, Reynolds has invested in 1Password, the Canadian cybersecurity startup; Wealthsimple, the online investment platform that reached a $5 billion CAD valuation in its 2021 raise; and holds a stake in Alpine F1 Racing as part of a celebrity investor group that paid a reported $218 million for a 24% stake. He also acquired a stake in Nuvei, the Canadian fintech firm, though that one resulted in a likely loss when Advent International acquired Nuvei in April 2024 at below his estimated entry price.

Not every Reynolds bet has worked. He's been honest about that. But the framework is consistent: find brands with authentic product quality, apply creative storytelling to build consumer affinity, and use his personal platform as genuine distribution.

What the Creative Operator Model Teaches Angel Investors

This is where Reynolds' approach gets genuinely instructive for early-stage investors. Most angels think of value-add in terms of introductions and advice. Reynolds models a different kind of value-add: showing up as an active creative contributor who changes what a company can do in the market. That's harder to replicate at scale, but the underlying principle matters. When you invest in a company, what can you genuinely offer beyond capital?

Eric Bahn, Hustle Fund GP, has talked about this in the context of operator-angels. The investors who get access to the best deals are the ones who have earned a reputation for actually helping. Reynolds built a $14 billion portfolio in part because founders and companies know what they're getting when he joins the cap table.

Angel Squad: Where Operator-Angels Learn the Craft

Angel Squad exists because most early-stage investors want to do what Reynolds does, add real value and back companies they believe in, but don't have a roadmap for how to start. With 2,500+ members across 50+ countries, the community teaches investors how to build genuine relationships with founders, identify companies worth backing, and become the kind of investor founders want on their cap table. Members invest alongside Hustle Fund in real deals, learning by doing. If Ryan Reynolds investments have taught you anything, it's that the best investors are the ones who bring something specific and irreplaceable to every company they join. Angel Squad helps you figure out what that is for you. Visit hustlefund.vc/squad.

The Takeaway

Ryan Reynolds investments work because Reynolds brings a genuinely rare asset to every company he backs: the ability to tell a story that makes people care. That's not something you can fake. But the broader principle applies to every angel investor: the best thing you can do for a portfolio company is bring the specific, unfair advantage only you have. Find that, and the returns tend to follow.