Shawn Cheng field notes!
Shawn Cheng | VC Hunted!

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Shawn Cheng #VCHunted Twitter Story – Who is the last dragon?

Having spent many years in the cryptocurrency space as an operator and founder, I was really looking forward to my conversation with Shawn. I know that there is so much going on in the decentralized world, and I wanted to get some fresh perspectives from Shawn. He did not disappoint!

Starting his career in startups, and a passion for helping companies tell their stories, Shawn had the awesome opportunity to work with companies such as Razorfish, BBDO, Charity Water, GE, Lowes, and HBO building their brands. Growing a robust network in NYC, and a growing interest in working with startups full-time, a friend connected Shawn to Gary Vaynerchuk, and the rest, you could say, is history:

“When I first met Gary he was a super angel, and his first investments were Facebook, Twitter, Tumblr, Uber, Birchbox. He know what would hit in the attention-economy. How do you convince someone who has everything to give you a shot? I just asked him what was his ‘big hairy problem,’ what kept him up at night, and what would really help his company.”

Shawn Cheng – VC Hunting S1E12
Shawn reminiscing on his love for Gary Vaynerchuk!
Gary is loving and kind, but also brings the hardcore.

What’s really cool about Shawn’s story is that not only was he successful in helping the Gary’s venture arm grow, but he was able to really learn from the best in the business. I really wanted to know if working with Gary was just like working with the ‘persona of Gary’ that I see on Tiktok and every other social media platform that he’s invaded. Is Gary wild and intense all the time?:

“Gary is a human personification of wine. He has tinges of love and joy and I don’t think people really realize that about him. He’s one of the most loving and caring people you’ll ever meet, and I think that’s actually one of the secrets to his success. People love working with him.”

Shawn Cheng – VC Hunting S1E12
Don’t ever forget the value of expanding your network!

Moving away from Gary Vaynerchuk’s awesomeness, I wanted to know if Shawn could share any lessons from helping Gary build his first $25M venture fund. What Shawn appreciated the most was being about to see thousands of deals, be surrounded by Gary’s powerful network, and learning to think probabilistically. In tandem with that, Shawn got to see how incubation of ideas and startups worked under Gary’s tutelage:

“[Working with Gary Vaynerchuk] I learned the value of networking. Your reputation is everything. This has led me to hopefully pick the right relationships with the right people to do business with and having long term gains with long-term people.”

Shawn Cheng – VC Hunting S1E12

Now, Shawn is engaged in the decentralized space. First, learning about cryptocurrency through Vayner/RSE venture fund by getting an allocation into Coinbase, the mother of all on-ramps for retail cryptocurrency in the United States. This was a great education in a leading decentralized finance company!

Is Bitcoin a scam? We laugh it off. Great technologies must prove themselves!

Going from Gary Vaynerchuk to Joe Lubin must have been one of the most interesting transitions in terms of leadership styles, communication styles, and personality types. I’ve personally not had the opportunity to meet either of them. But I have seen both of them in action. I could only assume that it must have been a very unique transition from being led by the hype-man in Gary, to the chill-man in Joseph:

“Both are brilliant men. They both have a vision of the world and a grit to make their vision into a reality that I respect so so much.”

Shawn Cheng – VC Hunting S1E12

I had to ask Shawn about where he sees cryptocurrency and decentralized tech going as we move into 2020:

“A hot topic now is decentralized finance. Be your own bank, as much or as little as you would like. Now we’re seeing an unbundling and people are moving from having no control to all of the control [over their finances]. There are a lot of areas of innovation that is happening in cryptocurrency, and when you put identity and your own personal data into the blender, those are all things we need to be paying attention to.”

Shawn Cheng – VC Hunting S1E12

It was great to speak more about the influence of Vitalik Buterin on the thesis of how ConsenSys deploys capital within the Ethereum startup world. Clearly the space is growing and it’s great to hear from someone on the ground like Shawn that the ecosystem is growing steadily. There really is so much innovation happening that is unseen by the public!

Finally, I wanted to ask Shawn if he’s ever considered growing his own fund. Having taken part in two very successful funds, I wondered whether he was up for the challenge, or pain of raising his own:

“I have but I think it’s too crowded right now. There is 24x the amount of funds in just the last 10 years… so is venture capital the best way in a world of tokenization?… Do you need to play by the same rules or is it more exciting to think about how value is being created and how do you distribute it properly based on the contributions?… A traditional fund? Probably not. A hybrid approach that takes advantage of decentralized finance, that sounds more interesting to me.”

Shawn Cheng – VC Hunting S1E12

This conversation deeply encouraged me that there are great people looking past the horizon at technology that will impact the world. Especially in a technology sector such as crypto, which still has a long way to go to mass-adoption, mass-appeal, and mass-usage.

But Shawn doesn’t want to destroy the world…

Maybe Ethereum will be the answer. Maybe it’s Bitcoin. All we know is that Shawn no longer believes that Daenerys Targaryen is his spirit animal and haircuts are worth paying for. 🙂

Paying for a good haircut is worth it. Or so I believe. I’m still on the $20 plan myself.

I look forward to checking in with Shawn again in the future, and I can’t wait to chat with some of his favorite startups from ConsenSys!

Enjoy my retrospective:

Shawn Cheng – Retrospective!

Peter Saddington

Shawn Cheng in the wild!


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This one counts as my kill!

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