Gaby Goldberg, online to on-chain
The 23-year-old investor is searching for the moments that will define web3.
Written by Meghna Rao
Photography by Allison Nguyen
Gaby Goldberg, a 23-year-old investor at early-stage consumer-crypto fund TCG Crypto, spent most of her pre-teen years selectively mute; she found herself unable to speak in many social situations, like school in Connecticut. Instead, she turned to the internet, where her online life soon grew rich. “Minecraft was the first place that I actually really felt comfortable,” she tells me over Zoom from Los Angeles. “It was this level playing field where I was judged only on what I brought to the table.”
She sold her Runescape account for real money. She ran a “California aesthetics” Tumblr. And, along with her brother, she moderated several communities on Minecraft.
By the end of high school, Goldberg had moved to Santa Barbara and started to make more offline friends. Her online and offline lives were distinct, except for the moments when she actively bridged them. “I took an AP History test one day and got on the Minecraft chat that evening,” she remembers. “Some people were talking about a test that had been so hard, and I picked up that it was the AP History exam. So I said, ‘oh my god, did you just take that test?’” One online friend, she soon learned, had taken the AP test, and was, like Goldberg, applying to colleges. And he became Goldberg's first online-to-IRL friend.
Goldberg’s hope for the internet — and one of her investment theses at TCG — is that web3 will make interactions like hers easier to access and more powerful when they happen.
At the heart of Goldberg's musings is an elusive question, one that's helped fuel a veritable (albeit rocky) gold rush. What sort of experiences will we have online on web3?
Goldberg is a popular Twitter follow, with more than 71K followers as of late July. But a little over two years ago, you wouldn't have seen Goldberg tweeting; she only joined Twitter in February 2020, at the behest of an investor she met while living in Tel Aviv on a sabbatical from Stanford, while she was working as an intern for human resources startup HiBob and writing about the Israeli tech ecosystem on her Medium. "He told me: 'you would get paid to do all of this stuff in venture,'" she remembers. "And he also said 'get on Twitter.'"
The pandemic hit; Goldberg started tweeting. She built up her following with daily “GM”s, short pieces of writing on Mirror, and community-building, from curating web3 reading lists to crypto jobs.
And Twitter began to pay off. She got her first job after coming across a tweet that early-stage seed fund Chapter One was hiring an intern; by October 2020, she had joined Bessemer Venture Partners, where she spent a year. And in September 2021, she joined TCG Crypto, an early-stage consumer crypto fund spun out of The Chernin Group, an investment firm that specializes in consumer brands in media and tech. Goldberg eventually did finish college, returning to Stanford to complete her degree in Symbolic Systems.
“If I could have picked my story, I would have operated first,” she says. “But crypto was moving fast and there was no way I was going to be able to catch up with people who were around during web1 and web2.”
At TCG, Goldberg focuses on finding consumer products for the “crypto-native” — those who are fully immersed in web3, like pre-teen Goldberg was in web2, when she joined Minecraft, ran communities, and made deep, online friendships.
“We define crypto-native as being on-chain, meaning you have a self-custody wallet, and you can engage directly with platforms and protocols in web3," says Goldberg. That is to say: a crypto-native doesn't just buy Bitcoin on a centralized exchange like Gemini or Coinbase; they have a wallet (like the Coinbase Wallet or Rainbow) where the ownership of the keys to their crypto assets remains with them — and not with a centralized entity.
It’s the natives that will display the signs of the future, explains Goldberg. “What I’m looking for is: what are the net-new consumer behaviors? How do we figure out how to support and shape them?”
According to Goldberg, web2 was great at getting us to spend lots of time online with our IRL friends and make some new online friends — but the puck has stopped there. On the other hand, the demand for more online-first experiences hasn’t stopped, whether people are taking and sharing screenshots across platforms or trying to figure out how to game the TikTok algorithm to push videos up.
These are the net-new consumer behaviors that Goldberg says she believes web3 can more easily solve for. And doing so will lead to the overall health of the internet.
“For example, because we’re not shareholders of Instagram, we’re realistically only incentivized to benefit ourselves,” she says. “That’s why you see people spamming the feed and using hashtags to hack their way in. It’s not about building a holistic community.”
TCG Crypto has publicly announced eight investments so far. The rounds they've participated in include a $1.5M seed round to Draup, a marketplace to buy, showcase, and rent out digital fashion, a $9.7M seed round to Arkive, the “world’s first decentralized museum,” and a $6.7M seed round to Cyber, which builds online experiences to showcase NFTs. Other investments include Ready Player DAO, Tribute Brand, Flamingo DAO, Rabbit Hole, and Altered State Machine.
With some of these investments, especially those that break traditional company structures like decentralized autonomous organizations (DAOs), TCG has had to unlearn traditional venture capital norms.
“If I could have picked my story, I would have operated first,” says Goldberg. “But crypto was moving fast and there was no way I was going to be able to catch up with people who were around during web1 and web2.”
Goldberg uses Flamingo DAO, a DAO that helps people invest in NFTs, as an example. In February 2022, TCG Crypto made an announcement that it had "joined" Flamingo.
“What does it mean to take a board seat in a DAO?,” Goldberg laughs. “It’s funny because we’re the ones who are pitching the DAO for the seat. We play a part in which assets are curated, how they think about liquidity, who else is going to join, how many seats everyone has."
Web3 has many things going for it, including evangelists like Goldberg, who are all-in on the technology. She believes in web3's success so deeply that she is planning for a future where the technology will be ubiquitous.
"I'm not really sure I'll send my kids to college because I'm pretty bullish on online credentialism," she says. "They might get a liberal education, maybe they'll focus on philosophy, but the rest of it — they’ll learn to build things online from day one. They'll build an identity around building these things. The things you do online are actually going to matter materially in online and offline spaces.”
And there definitely isn't a lack of money flowing into the space. Coinbase Venture’s $2.5B fund has made at least 269 investments so far; Andreessen Horowitz raised a $4.5B crypto-focused fund in March 2022; and TCG, too, is raising a purported $1B fund that will include its web3 investments.
Instead, the issue with crypto seems to be the very nature of most dreams — it's speculative, and speculations aren't built on solid foundations.
What if it all fails? Goldberg is not too worried.
“Your appetite for risk is almost like a muscle that needs to be trained," says Goldberg. "Train it. If you don't train it, you lose that muscle, and you miss that opportunity.”
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