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Lex Sokolin – from Standup Comic to Generative VC

When Lex Sokolin began speaking at conferences, he tended to be the only bright spark – a young person on stage in a myriad of soulless events hosted in the basements of hotels and earmarked by beige carpets. Middle level banker levels of seriousness – and boredom – crushed these events. As a natural introvert, speaking out did not come easily and certainly not in such serious events.

“It felt as though I might be a rookie stand-up comedian,” says Sokolin. “And so, I began to approach these panels and speaking roles with humour. Since then, it’s been a blast and I love conferences now and hope people remember me with fondness for injecting humour into what might otherwise be dry content.”

It works. Having witnessed him on a stage at a Web3 event in London, I can’t remember what he said, but I do remember laughing. It’s not quite Maya Angelou but it’s close. *

Sokolin has been balancing two careers for the past 15 to 20 years which belies his youthful appearance. A solid 40 years’ old now he began building websites in 2002. At that stage it was called New Media and included exciting innovations such as Flash animations. Separately he went through traditional finance training, and since he was living in New York, he gravitated towards Wall Street.

“I was an immigrant and so I studied economics. I got an MBA and built a skill set around asset management and investment banking. The two threads of my career were not very compatible, at least not when I was younger, but over time they have started to amalgamate.”

Sokolin began his formal career at Lehman Brothers in 2006 and found the firm’s iconic bankruptcy to be definitional rather than devastating. Sokolin says he learnt from it, moving imperceptibly from Wall Street into Fintech. By 2012 he was working in a startup culture and learning not, as he says, to polish turds. Cue laughter from the crowd again.

“Actually,” he corrects himself smiling, “I learnt not to put scotch tape on broken projects. More profoundly I was exploring modern distribution of traditional financial products. For example, putting access to finance on a phone or a website. It’s a reductive way to look at NeoBanks and payment systems.”

He took a few years to build a FinTech practice for an equity research firm but increasingly became more interested in the big platform shifts around 2017 into crypto, AI, AR and VR. At that stage they were still disconnected, but Sokolin began to wonder how they might change finance and money.

“This is always my question, and moreover, how might they change the big public banks, how might payments exist in a virtual world and how will AI underwrite financial products.”

This wondering led him to join Consensys in the heart of the previous bear market. Ethereum was priced at $80 and things were just on the verge of falling apart. After a number of stints on digital assets strategy, followed by enterprise blockchain, he was moved to the area of DeFi where he was asked to run the marketing team around Metamask and to build out a crypto economics team.

“I was the chief economist for about a year and a half.”

When asked if these were disparate and quite separate roles, Sokolin thinks for a moment.

“My career has been less functional and more about themes. So, it’s the interplay between creativity, art and novelty and then integrating financial services. For the four years I worked at Consensys I kind of touched everything from community, to financials, to tokenized incentives, to ecosystem design right through building business apps.”

At the same time, as the industry seemed to be falling apart, Sokloin questioned his presence. He began to rebuild his thesis for the space and to find his confidence again. That was what brought him to the investment thesis for generative ventures.

As Sokolin explains he came to crypto from finance, and was enamoured with the new financial structures, DeFi and access to new digital asset classes. But he cautions that Web3 only works if there is economic activity and if finance is subservient to that economy.

“Finance cannot be its own economy.”

The smallest benefit of AI can be to create productivity gains, but on the other side the opportunities are infinite. Sokolin sees a huge machine network for financial activity and machine created objects coming from generative AI.

“And my hope is that they are going to be owned and transacted in Web3.”

Sokolin has created a fund to support generative ventures. He’s created a North Star vision which looks out to 5 to ten years from now. He sees it as a contrast of concentric circles of Web3, AI and Fintech where companies are focused on economic activity rather than pure economic financial gain. He lists off a series of companies with which he is seriously considering getting involved. These range from security and stablecoin payments, to commercial applications and payment processing. He sees the overlap between AI and crypto, where people are building out autonomous agents to take actions on people’s behalf.

“It sounds more fancy than it is.” He laughs.

Sokolin launched Generative Ventures, an engaged venture fund focused on the machine economy, in July 2023, and has spoken with around 500 companies in the first three months alone. The fund has invested in a number already and is less interested in the exit than the joy of discovering an emerging machine economy where machine labour comes from AI.

“It’s not a pure play crypto fund. It’s not a pure AI fund. It’s not a pure play fintech fund. I call it the economic architecture of the metaverse.”

Sokolin carries on saying it’s not the games, not the NFTs and not the glitzy rendering stuff.

“That’s our qualitative filter. I think there are mercenary funds out there that prioritise a quick trade and lots of leverage. But the terrible outcome of short-term mercenary capital space was highlighted in 2021. We’ve learnt the lessons and life is just too short.”

Finally on the topic of tokens in Web3.

“This is probably a slightly radical view but if you are not doing tokens, you really shouldn’t be in Web3. The whole point of Web3 is tokens, ownership, community and participation incentives and you’re missing the whole point of the architecture if you don’t do tokens!”

*“I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel,” Maya Angelou.