Jack Dorsey on a laptop screen
Photo: Daniel Acker/Bloomberg via Getty Images

Square now has a full-time CEO. What does that mean for its crypto strategy?

Protocol Fintech

Hello and welcome to Protocol | Fintech! This Tuesday: What Square looks like with a bitcoin-focused Jack Dorsey at the helm full time, why giving crypto is still so hard, and the latest challenges facing “buy now, pay later.”

Bitcoin Jack is at the wheel

Jack Dorsey is leaving Twitter. That means more time to spend on Square, where he can feel free to crypto to his heart's content.

Under Dorsey, Twitter kicked off initiatives to research decentralized social media, and even hired a head of crypto recently. But it’s hard to imagine that those efforts’ glacial pace pleased Dorsey. Twitter wouldn’t even change its policies to let it hold bitcoin, an indication of where it really stood on crypto.

Dorsey, meanwhile, has been increasingly vocal about his obsession with bitcoin and has focused Square clearly on crypto — where the technology is a better fit anyway.

"Whatever I can do, whatever my companies can do to make bitcoin accessible to everyone is how I'm going to spend the rest of my life. If I were not at Square or Twitter, I'd be working on bitcoin," Dorsey told a crypto conference in Miami this summer. The only thing that seems to have changed is whether Twitter fit in that picture.

Dorsey has increasingly steered Square into crypto territory. While other fintech companies are happy to just tack on crypto trading, Square has gone much deeper.

  • In July, Square said it was working on a hardware wallet. It's not an obvious fit for Square’s mainstream audience, but it could help build credibility with more sophisticated crypto users.
  • Soon after, Dorsey announced TBD, a new unit within Square to build developer technology for crypto. TBD aims to build future-looking crypto services, such as the recently announced tbDEX, a decentralized bitcoin exchange that enables people to transact using different levels of identity verification, which could be very low or very high depending on individual preferences, or legal or regulatory issues.
  • Ironically for a decentralized technology, exchanging crypto for fiat often goes through centralized exchanges like Coinbase. “You can think about this as a decentralized exchange for fiat," TBD's Mike Brock wrote on Twitter.
  • Expect more broad, industrywide attempts from Square to make the company more of a crypto leader.

Square’s future is crypto — but that could mean many things. Square already has a large, traditional payments business throwing off cash from traditional fiat transactions. Steering the ship toward crypto may be tough.

  • Cash App offers the clearest indication of crypto’s potential for Square. It’s proven a popular way for crypto newbies to dabble in bitcoin.
  • What about the rest of Square, which includes payment processing, lending and payroll? Any of those services could include crypto — but should they? And will Square’s small-business customers even be interested?
  • One scenario: Square uses its existing payments business to fund crypto moonshots until they become self-sustaining.
  • Another scenario: Square invests to rebuild its existing businesses around crypto — a riskier scenario, but one that could better leverage the company’s reach to accelerate crypto adoption.
  • If you’re a product manager at Square and you want to impress the boss — who’s going to be around more in 2022 — you’d best be thinking about where crypto fits in.

With the Twitter millstone lifted from his neck, Dorsey is likely to become even more of a crypto personality. He won’t need to feign interest in those boring Congressional hearings! He’s already a marquee name on the crypto conference circuit, where his bitcoin maximalist stance draws controversy and attention. And he’s made angel investments in crypto startups. If anything, the Twitter move is a signal that Square had best rebuild itself around crypto before its fickle leader jettisons it in favor of an even more crypto-forward vessel.

— Tomio Geron (email | twitter)


The future of financial services will be built on the digital experience as industry leaders look to innovate, drive operational agility, top-line growth and security at scale. VMware is helping organizations accelerate digital-first banking on a trusted foundation with multi-cloud services for all apps.

Learn more

From Protocol | Fintech

“Buy now, pay later” is booming, but companies are facing pressure to change. U.S. regulators, worried about consumer debt and unregulated credit, could force companies to rein in practices that have turbocharged their growth.

The pandemic keeps changing ecommerce.That makes fraud harder to fight. As the second holiday season under COVID-19 gets underway, fraud finds new forms.

It’s still too hard to give crypto this holiday. Here's how the industry Scrooged itself out of a big opportunity.

Coming up

China’s fintech future: Join the Protocol | China team to hear about Beijing’s latest moves to test a CBDC and in-country fintech innovations with promise for global adoption. Protocol’s David Wertime moderates an expert panel on Thursday, Dec. 2, at 10 a.m. PT/1 p.m. ET. Reserve your spot now.


“I wouldn’t convince him to invest in crypto. I think it’s not necessary that everybody has to invest in crypto.”Binance CEO Changpeng Zhao on whether Warren Buffett should invest in digital tokens.

“Robinhood has this situation where they’re always in a crisis 6 to 18 months ahead of where their operations are. This hack is an example of it.” —Mazi Bahadori, chief compliance officer of Altruist, on the big data breach at the online brokerage.

“When I speak with regulators, and they ask about decentralization, I tell them that the real measure of decentralization is censorship resistance, not distribution. Everyone is learning here, and they definitely are still a ways off from truly understanding.” Joseph Weinberg, co-founder of Shyft Network.

3 questions with Forge Global CEO Kelly Rodriques

What fintech trend are you most excited about?

I've been watching carefully the emergence of blockchain and digital asset technology. Those types of technologies can efficiently and rapidly expand to a global market and will help ensure that what we do (facilitate private securities trading) reaches that global market. But that technology trend has been on its own track and has been trying to get traction and is really just starting to gain acceptance by governments and regulators all around the world. So we're really excited about developments there and that’s a sector we'll continue to watch.

What fintech trend is most troubling for you?

I've been watching fintech for 15 years and what bothers me today is related to the gig-economy phenomenon. When I see the exploitation of consumers around things like surge pricing, it really bothers me. I think a solution for this kind of problem is competition and I think as consumers become disillusioned by being exploited over surge pricing, we’ll start to see disruption from innovators who can create better product-market fit. I understand that there is some relationship between supply and demand, but I just don't see a world where people accept surge pricing indefinitely.

What's your favorite pastime that doesn't involve a screen?

I have a recreational infatuation with motorcycles of all kinds, from big cruisers to hogs to race bikes. I'm on a motorcycle every weekend.

Need to know

Revolut is acquiring Nobly. The digital bank said the point-of-sale software company will help it expand in the restaurant and hospitality sectors.

Mastercard and Jeeves formed a partnership focused on Mexico. The payments giant has teamed up with the Mexico-based expense management and banking company to launch a multicurrency card.

Sen. Sherrod Brown has asked for information from stablecoin issuers. The issuers include Coinbase, Tether, Circle, Gemini, Binance US, Paxos, TrustToken and Centre.

Making moves

Puneet Singhvi was named Citi’s head of digital assets for its institutional group. She was previously head of blockchain and digital assets for the bank’s global markets team.

Mark Cuban and Kevin Hart invested in Jackpocket. The lottery app raised a total of $120 million.

Deal flow

Royal raised $55 million. The NFT music rights startup's series A round came from Andreessen Horowitz’s crypto investment arm.

Thought Machine raised $200 million. The cloud banking software company’s series C round was led by Nyca Partners.

Jefa raised $2 million. The digital bank geared toward women in Latin America and the Caribbean raised a seed round from investors including the Venture Collective, partners of DST Global and Foundation Capital.

Slice raised $220 million. The India-based card-issuing software company’s series B round was led by Tiger Global and Insight Partners.

Settle raised $60 million. The cash flow management startup’s series B round was led by Ribbit Capital.


The future of financial services will be built on the digital experience as industry leaders look to innovate, drive operational agility, top-line growth and security at scale. VMware is helping organizations accelerate digital-first banking on a trusted foundation with multi-cloud services for all apps.

Learn more

Data point

$8.9 billion: That’s the amount online shoppers spent on Black Friday, down from $9 billion in 2020 — the first ever year-over-year decline, according to Adobe Analytics.

Update: An earlier version of this newsletter misidentified an investor in Jefa. Partners of DST Global invested in the digital bank.

Thanks for reading — see you Friday!

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