Legal Foundations for Stablecoins in 2025: Interview with Andrew Jacobson

Main Takeaways:

• Clear regulation is critical for innovation: startups need legal predictability to build rather than waste resources on conflicting legal advice.
• Non-custodial infrastructure is the future of DeFi: users should control their assets directly, and education will be key to helping mainstream audiences understand this.
• Stablecoins will power small-dollar payments: expect sub-$300 transactions like groceries, subscriptions, and tipping to increasingly move to stablecoins.
• A new wave of infrastructure is coming: with regulatory clarity on the horizon, the next three to four years represent a once-in-a-generation moment to build within the stablecoin space.
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This interview features Andrew Jacobson from Halliday, a company working to create a unified, cross-chain payments ecosystem with tools like Halliday Payments. Halliday uses the Workflow Protocol to streamline complex workflows and enable seamless multi-chain, non-custodial access to digital assets. With deep experience advising both startups and regulators, Andrew shared sharp, practical insights on compliance, legal innovation, and the future of stablecoin adoption.

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Halliday’s User-First Approach to a Multi-Chain Future
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Q: Could you start by giving us an overview of what Halliday is building and your role?

I'm the General Counsel at Halliday. We're building infrastructure that makes it easier for users and developers to access any token on any chain, with a strong emphasis on non-custodial access and decentralization. Our core technology is built on the Workflow Protocol, which allows developers to safely involve AI and third parties in complex onchain workflows. We believe that in order to scale the next generation of applications, the complexity of crypto needs to be abstracted.

As General Counsel, my role is to ensure that we’re building in a way that is legally sound and aligned with our long-term vision. That means working closely with our product and engineering teams, helping shape the strategic direction of our infrastructure, and creating space for innovation while maintaining compliance.
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Q: Why prioritize non-custodial architecture?

Crypto, for all its innovation, remains complex and often misunderstood by most users. Many people still do not fully understand how custody works, who actually controls their funds, or what risks they are taking on. This lack of clarity creates friction and slows down adoption.

At Halliday, we believe the future of crypto depends on user empowerment, and that starts with self-custody. Non-custodial architecture gives users full control over their assets, which is essential for building trust and driving long-term engagement. We see this model as the foundation of a healthier and more resilient financial ecosystem.

Regulation: A Double-Edged Sword for Stablecoin Innovation
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Q: How do you see clear regulatory frameworks fostering innovation in crypto?

Regulatory clarity is a foundational requirement for innovation. Builders need to know the rules of the road in order to create confidently and sustainably. When the legal environment is murky or constantly shifting, it becomes extremely difficult for founders, engineers, and product teams to launch or scale with any certainty.

In the United States, the absence of a unified federal framework has resulted in a highly fragmented landscape. Startups must contend with a complex mix of state-level regulations, federal oversight, and inconsistent interpretations of existing financial laws. This creates confusion and often leads to startups spending significant resources on legal consultations, only to receive vague or conflicting advice.
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Q: What’s been your experience navigating those complexities?

I have been advising crypto startups for nearly a decade, and one consistent theme has been the overwhelming legal burden that founders face. In many cases, legal expenses end up matching engineering costs, which is an incredibly inefficient use of capital for an early-stage company. Instead of funding innovation, companies are forced to pay law firms to interpret a constantly evolving set of rules.

What makes it even more frustrating is the inconsistency. You can ask three different lawyers the same question and receive three different answers, none of which give you the certainty you need to move forward. This lack of clarity slows down progress and discourages risk-taking.

Stablecoins are a great example of where clear and consistent regulation would make a meaningful difference. These are products that already operate at scale in many jurisdictions, and yet the uncertainty in the United States creates unnecessary friction. With more predictable rules, founders could build with confidence, focus their resources on product development, and contribute more directly to the growth of the ecosystem.
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Q: What barriers still stand in the way of scaling stablecoin-based payments?

The biggest barrier is regulatory fragmentation. In the United States, launching a compliant crypto or stablecoin product requires navigating a maze of different agencies and jurisdictions. Companies must account for state regulators, federal securities laws, banking laws, and a range of overlapping rules that often contradict or conflict with one another.

Earlier in my career, I worked at the New York Department of Financial Services, including during the development of the BitLicense. While that was a meaningful first step toward crypto-specific regulation, the broader landscape remained fragmented. As a result, many of my clients at the time made the strategic decision to build in Europe or Asia first. They saw those markets as more navigable and more supportive of innovation. The United States lost valuable ground during that period, both in terms of talent and market leadership, although fortunately that trend seems to be shifting.

A Vision for the Future: Stablecoins as a Part of Everyday Life
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Q: What use cases for stablecoins do you think are most scalable long-term?

Over the long term, I believe that small-dollar payments will increasingly be powered by stablecoins. Transactions under three hundred dollars, such as paying for groceries, subscriptions, or sending a tip, are well suited for stablecoin rails. These payments benefit from instant settlement, minimal fees, and a digital cash experience that traditional systems are often unable to deliver efficiently.

What makes stablecoins especially compelling is their programmability. Unlike static forms of money, stablecoins function as software. This allows for automation, customization, and integration into complex workflows. Whether it is setting smart allowances, building recurring payment systems, or enabling conditional transfers, programmable money introduces an entirely new way to manage and move value online.
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Q: What will it take to get there?

Consumer education is absolutely essential. Today, most people still view crypto primarily as an asset class. They focus on price movements, market cycles, and speculation, rather than understanding the underlying infrastructure that powers it all. Helping people shift from thinking about crypto as just an investment to seeing it as foundational infrastructure is a critical step.

When users begin to understand the benefits of peer-to-peer systems, programmable money, and decentralized networks, the value proposition becomes much more compelling. As traditional financial institutions continue to explore and integrate crypto, that mindset shift will happen more naturally. The combination of better education and increased visibility from trusted players will accelerate adoption in a meaningful way.
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Building with Compliance and Integrity
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Q: How do you build a compliance strategy that can evolve with changing regulations?

It starts with principles. The foundation of any strong compliance strategy should be rooted in values that stand the test of time, even as specific laws and guidelines evolve. One of the most important principles is not enabling illicit activity. That means building systems that are transparent, secure, and resistant to abuse.

Just as important is the culture within the company. You need to create an environment grounded in integrity and a high standard of excellence. Compliance is not just about checking boxes or meeting minimum requirements. It is about doing right by the user and considering their safety, rights, and expectations in every product decision.
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Q: What advice would you give to a fintech startup entering the stablecoin space?

Start by hiring high-integrity people. The tone and values of a company are set from the top, and those early hires will shape both your internal culture and your external reputation. From there, set clear guardrails. If your project involves token issuance or onchain incentives, define in advance what insiders and affiliates are allowed to do with those tokens. Transparency and discipline in this area go a long way in building trust with your community and avoiding reputational risk.

You should also prioritize user protection. This includes thinking through what rights users have, what risks they may face, and how your product design can minimize those risks. Above all, remember that in Web3, the community is the foundation of your product. The projects that succeed are the ones that truly center their users. The ones that do not often struggle to gain traction or fail to recover from missteps. Trust is everything in this space and it has to be earned.

The Evolving Role of Legal in Crypto Companies
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Q: How is the role of General Counsel evolving in Web3 infrastructure companies?

The role of General Counsel in a crypto company is about helping accelerate the business while also protecting it. Those two responsibilities go hand in hand, and both are essential for long-term success in an evolving regulatory environment.

To do that effectively, a General Counsel cannot operate in a silo. They need to be embedded alongside product and engineering teams, involved in decision-making from the start, and closely aligned with how the company builds. Speaking the language of engineers is critical. It helps legal teams become true partners in the development process rather than perceived blockers.

Ultimately, the General Counsel should serve as both a business enabler and a safeguard. By deeply understanding the technology and working side by side with the builders, they can guide the company through legal uncertainty while ensuring that product development stays fast, thoughtful, and compliant.
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Q: Any final reflections as the space heads into its next growth cycle?

Now is the time to build. I have been telling engineers to revisit the projects and ideas they had to abandon over the past few years due to excessive regulatory pressure. Many of those ideas, such as privacy tooling, were paused not because they lacked potential, but because the landscape was too uncertain to support them.

That moment of constraint is coming to an end. What lies ahead is a once-in-a-generation opportunity to reset, rebuild, and push the boundaries of what this technology can do. The industry was held back by unclear rules, adversarial enforcement, and an environment that made developers hesitant to take risks. But we are entering a new phase: a structural shift toward crypto as infrastructure, and it will define the next decade of innovation.

Anyone building today has a chance to shape that future.
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About Andrew Jacobson: Andrew Jacobson is the General Counsel at Halliday.  Andrew joined Halliday after nearly three years as Global Head of Legal at 21.co and 21Shares, one of the world’s largest crypto asset managers and blockchain infrastructure companies.  During that time, Andrew launched the first spot BTC ETF in the US and grew AUM to over $10 billion, scaling a global legal, compliance, risk, and regulatory affairs function.  Andrew previously served as an enforcement attorney at the New York State Department of Financial Services and built the blockchain legal practice at Seward & Kissel LLP.