The three most powerful figures in the history of crypto VC, even Dragonfly's partners are humbled by their abilities.

Author: Haseeb >|<, Partner at Dragonfly

Compiled by: Deep Tide TechFlow

LPs sometimes ask me who I consider to be the best venture capitalist in the crypto space.

I've thought about this a lot.

Since I started venture capital in the crypto space, I've always aspired to be the best. I'm passionate about competition, and investing is the purest form of competition. Only one person can win a deal, and only one person can pick the winner of this cycle.

But when you examine them honestly and do a thorough calculation, you'll find that three people have proven themselves to be the "GOAT" of crypto venture capital.

This might seem a bit like hype (which it is), and it might not appeal to those who aren't crypto VCs. But I am a crypto VC myself. This article is dedicated to those of us who see it as a lifelong career.

Here are my top three crypto venture capital investments of all time.

#3. @danrobinson ( @paradigm )

There's a legendary story about Mike Speiser, managing partner of Sutter Hill Ventures. He incubated Snowflake, which later grew into a $75 billion company. It's almost unheard of for a venture capital firm to create such immense value for its portfolio companies.

Dan Robinson is the Mike Speiser of the crypto world.

Time and again, Dan stands at the starting point of generations of great companies in the crypto space. He was involved from the very beginning of Uniswap, and was in fact a co-author and foundational contributor to Uniswap V3, which became a core pillar of on-chain spot trading. He also played a key role in the early stages of Flashbots, which pioneered the modern MEV (Maximum Extractable Value) auction model. He was also a contributor to early research on Plasma (the precursor to modern Rollups), which ultimately led him to lead Optimism's seed round funding.

Dan is a truly multi-talented individual. He has broken the mold of traditional venture capital. He started as a securities lawyer, then became a self-taught protocol architect and mathematician, and now a self-taught investor. Perhaps the greatest investment @matthuang (co-founder of Paradigm) ever made was hiring Dan. Whenever we lost out to Paradigm, many times people would say, "You guys are great, but I'm sorry, I have to work with Dan."

The most awe-inspiring investors are those who do more than just invest. Dan consistently sees where things are headed and has personally driven progress on numerous occasions. This is precisely why he is one of the greatest investors in the crypto space, earning him a place on the "crypto Mount Rushmore."

#2. @cdixon ( @a16zcrypto )

Chris Dixon is the "OG of OGs" (OG stands for Original Gangster) in the crypto world. He saw the potential of crypto much earlier than anyone else. Before Chris, crypto venture capital was still in a "small league" stage.

He was the first mainstream venture capitalist to publicly commit to the crypto space and bet his entire career on it. He pioneered the use of venture capital language in conjunction with crypto and internet investing, and popularized these concepts in Silicon Valley and among the institutional LPs (Limited Partners) behind it. Many of the concepts we discuss daily on our Investment Committee (IC) are directly borrowed from Chris. It's no exaggeration to say that I'm now on the same path Chris initially laid out for himself.

Two deals spearheaded by Chris Dixon are considered milestones in crypto venture capital history. The first, of course, is Coinbase. In 2013, Chris led Coinbase's Series B funding round, when the entire industry was still in its infancy and the future was uncertain. This deal perfectly embodied Dixon's investment philosophy—"What the smartest people do on weekends is what everyone will be doing ten years from now." He foresaw the deal and subsequently doubled down, dedicating himself entirely to the industry. Doing what we're doing now was far more difficult in the era when Chris first did this.

The second deal was with Uniswap. Almost everyone who saw Uniswap's Series A funding round backed out (Uniswap's fully diluted valuation was $100 million at the time—Uniswap was very small then). There was much debate in the industry about whether AMMs (Automated Market Makers) were capital-efficient enough, whether they faced excessive adverse selection, and whether they were easily replicated. Paradigm (despite leading the seed round) withdrew, and so did we; reportedly, the rest of a16z's investment committee were also unwilling to participate in the deal.

But what about Chris? He reportedly said, "A smart contract that can buy and sell anything? Sounds pretty cool. Who knows what might happen—let's do it." He turned out to be right. It really is cool. It's precisely the possibilities offered by permissionless AMMs that have spawned so many non-obvious innovations. After missing out on this Series A funding round, I learned an important lesson.

While I disagree with a16z's worldview on many fronts, everyone in the industry should have deep respect for Chris. He is one of the biggest contributors to the crypto industry's current cultural standing, having fought against resistance in Washington throughout his career to legitimize crypto and gain cultural acceptance as a cutting-edge technology. Much of our language and expressions about crypto comes directly from Chris.

Without Chris Dixon's early contributions, crypto venture capital would never have reached its current state. For that, we should be deeply grateful to him.

#1. @KyleSamani ( @multicoin )

Kyle, Kyle, Kyle.

I often argue with Kyle. He makes a lot of people—including myself—uncomfortable, and this happens almost constantly.

But investing is like a competitive sport. Ultimately, you either score points on the scoreboard or you don't.

Kyle scored the most points. The incredible returns he made from Solana's seed round investment, and the effort he put into the deal, will surely be the subject of a book in the future, one that I'll probably read with a furrowed brow.

You see, the best investors are contrarian thinkers, and Kyle is a true contrarian thinker. Being a contrarian thinker doesn't mean you publish a controversial opinion that gets a bunch of people exclaiming, "Wow, that's so smart!" If everyone wants to share your opinion, then by definition you're not a contrarian thinker. You'll know you're a true contrarian thinker when you make people angry, make them think you're stupid, or even make them think you're burning money.

Kyle is one of the few truly contrarian thinkers in the crypto space. I disagree with him on almost everything. But his initial investment in Solana, and his unwavering belief in holding Solana after the FTX crash, undoubtedly makes him one of the greatest venture capitalists in crypto history.

We often say that venture capital follows a power-law distribution. Kyle and his legendary Solana investment are the best example of this. Sometimes, all it takes is a single deal.

That's why Kyle is the greatest crypto venture capitalist of all time.

So, these are my top three.

LPs sometimes ask me where they think they would rank on this list.

While I rate myself very highly—yes, extremely highly—I don't think I'm in the top three. I'm definitely in the top ten, maybe even in the top five, but I'm not as good as these three. I hope that one day, before I finish my career, I'll surpass them. If we're talking about quarterly performance, I do have some quarters where I outperformed each of them.

But overall? These three are the best of all time.

For Dragonfly, praising competitors might not be very helpful. But there's something more significant than competition. You see, being an investor in this industry is tough—most of my peers along the way didn't make it. The crypto space is brutal.

Although I compete with these individuals every day, I have immense respect for them. I've witnessed their growth through nearly a decade of ups and downs. We've all weathered the storms of the crypto space together, supporting our founders, supporting the industry, and helping it reach a level comparable to other technology sectors. In my year-end reflections, I feel it's worthwhile to pay tribute to them in an industry that rarely sings praises of venture capitalists.

Whether they know it or not, everyone has contributed a great deal to me. I have learned so much from each of them. I sincerely hope they are proud of what they have accomplished.

Dan Robinson saw it most clearly.

Chris Dixon was the first to see it.

Kyle Samani saw it all the way through.

Salute, gentlemen. May our exciting competition continue.