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

Gary Vaynerchuk grew up in the Soviet Union, immigrated to the United States at age three, and spent his childhood selling lemonade, baseball cards, and flowers he picked from neighbors' gardens. By his mid-twenties, he had taken his father's New Jersey liquor store from $3 million to $60 million in annual revenue by doing what nobody else in the wine industry was doing: creating daily YouTube content in 2006 and building an actual community around it. That playbook, identify underpriced attention, build audience, convert to business, became the lens through which he has evaluated investments ever since. Gary Vaynerchuk investments are the direct output of someone who has spent thirty years thinking about where consumer behavior is heading before the market consensus catches up.

From Wine Library to Silicon Valley Angel

The angel investing started around 2009, the same year he launched VaynerMedia with his brother AJ. His first three checks went into Twitter, Facebook, and Tumblr. All three were bets on platforms that were building new consumer attention surfaces, which is exactly what he had done at Wine Library TV. The logic was straightforward even if the timing was extraordinary: these were the places where people would spend their time, which meant they were where brands would eventually need to be, which meant the companies behind them would be worth a lot of money.

He followed those early checks with investments in Venmo, Snapchat, Coinbase, and Uber. He has been open about missing Uber's first round and calling it one of his biggest investing mistakes, eventually investing in a later round after his brother took the first Uber ride in New York City in 2011. The portfolio now covers over 176 investments according to PitchBook, with 37 documented exits. Empathy Wines, which he co-founded, was acquired by Constellation Brands in 2020. Resy, the restaurant reservation app he co-founded, was acquired by American Express in 2019.

The Attention Framework in Practice

What distinguishes Gary Vaynerchuk investments from most celebrity angel portfolios is how consistently they reflect a single underlying thesis. He has not chased sectors or technologies. He has chased attention. Every major early investment traces back to a platform or product that was building a new surface area for consumer attention before mainstream adoption.

Twitter in 2009 was where the internet's most influential voices were gravitating before brands understood it. Snapchat was where teenagers were spending time before advertisers figured out how to price it. Coinbase was where early crypto adoption was concentrating before institutional capital arrived. The through-line isn't technology or fintech or social media. It's the pattern of recognizing where attention is moving before the pricing reflects it.

Eric Bahn, Hustle Fund GP and co-founder, has noted that the investors who consistently find early-stage winners are usually the ones with genuine consumer insight, not just financial pattern recognition. VaynerMedia, which generates nearly $300 million in annual revenue serving Fortune 500 clients on social media strategy, is essentially a machine for developing that consumer insight at scale. It gives Vaynerchuk a practitioner's perspective on where attention actually lives, updated in real time, that most VCs simply don't have.

Recent Activity and Current Positioning

His latest investment as of January 2026 was in The 33rd Team, a sports analytics and media company. Before that, he backed Pro Padel League in March 2025, continuing a pattern of investing in emerging sports properties and media at early stages. The board seats he currently holds include Gymshark, Bojangles, MaryRuth Organics, and Tracer, an advertising measurement company. These aren't passive positions. He actively applies his marketing and brand-building expertise to each.

VeeFriends, his NFT project launched in 2021, reflects the same attention-first logic applied to the Web3 cycle. Some of those bets held up better than others as crypto markets cooled. But the underlying behavior, identifying emerging consumer attention surfaces early and getting positioned before pricing normalizes, has been consistent throughout.

Elizabeth Yin, Hustle Fund GP, has been direct about the importance of investors understanding what they're genuinely good at evaluating and staying inside that lane. Vaynerchuk has been remarkably consistent on that front for fifteen years.

Angel Squad: Building Your Own Attention Edge

The lesson from Gary Vaynerchuk investments isn't just about picking consumer platforms early. It's about developing the kind of genuine market insight that comes from being deeply embedded in a domain. Angel Squad brings together 2,500 investors across 50 countries, many of them operators-turned-angels who bring exactly that kind of domain expertise to their deal evaluation. Members invest alongside Hustle Fund, build real portfolios, and develop frameworks for finding deals that others are overlooking. If GaryVee's playbook resonates, Angel Squad is where you start translating that intuition into a disciplined investment process. Learn more at hustlefund.vc/squad.

The Takeaway

Gary Vaynerchuk investments work because he built a professional operation that generates proprietary insight into consumer behavior and then deployed that insight systematically in his angel portfolio. He wasn't smarter than everyone else about Twitter or Snapchat in some abstract analytical sense. He was more embedded in how those platforms were actually being used. That's an edge available to any investor who takes their domain knowledge seriously and has the discipline to act on it before the market catches up.