Dave Rodman, Managing Partner, The Rodman Law Group – Interview Series

Dave Rodman, Managing Partner, The Rodman Law Group, is an attorney whose career has focused on emerging and highly regulated industries, including digital assets, Web3, cannabis, psychedelics, and venture capital. As head of the firm’s emerging companies and venture capital practice, he advises founders and investors on corporate structuring, financing, securities law, intellectual property, regulatory risk, and transactions from formation through exit. Rodman has facilitated more than $1 billion in financing and corporate transactions, combining his legal experience with the practical perspective he gained as a founder to help clients evaluate complex legal and business risks.

The Rodman Law Group advises founders, investors, funds, and companies operating across Web3 and the digital asset ecosystem. Active in the sector since 2016, the firm supports clients with corporate structuring, token offerings, venture financing, investment funds, securities law, intellectual property, regulatory compliance, transactions, and dispute resolution. Its work spans decentralized finance, non-fungible tokens, decentralized autonomous organizations, blockchain infrastructure, fintech, and other emerging financial technologies, with an emphasis on helping clients navigate the legal and jurisdictional complexities associated with building and investing in digital asset businesses.

You’ve spent your entire legal career working in nascent and highly regulated industries, from cannabis to digital assets and venture capital. How did those early experiences shape your approach to advising founders in today’s rapidly evolving Web3 and crypto ecosystem?

I think my early experience learning to be a lawyer in a space where the underlying economic activity was federally illegal shaped the way I approach both the law and my clients. It gave me a strong understanding of my clients’ needs and how to help them evaluate their options across a broad spectrum of legal and business risk.

Traditional lawyers who entered Web3 often had a much more rigid approach. At least initially, many weren’t willing to think outside the box for founders operating in these emerging industries. When I started practicing Web3 law, it actually felt like a de-risking exercise. The underlying activity wasn’t federally illegal.

To be clear, I was never intimidated by cannabis being illegal, but I was able to jump into crypto with both feet while many others were still cautiously testing the waters. It was interesting to watch the evolution of both industries as large law firms eventually became comfortable enough to enter the space and began marketing themselves as experts. I always found myself thinking, “Where were you when this industry was just getting started?” Many of them were standing on the sidelines.

You’ve facilitated over a billion dollars in financings and transactions across emerging sectors. What are the biggest differences you see between traditional venture deals and capital formation in the digital asset space?

Speed. There is no question.

Everything in crypto operates in what feels like speed run mode. I’ve never seen companies get founded, funded, and reach valuations in the hundreds of millions of dollars so quickly. It has been genuinely astonishing.

What also stands out is the remarkably casual attitude toward transactions involving enormous sums of money. I’ve seen deals worth a few hundred thousand dollars in the traditional world take months to close. Meanwhile, I’ve worked on transactions worth hundreds of millions of dollars that opened and closed in about two weeks, with everyone involved complaining that the process was taking too long.

My favorite example is the single largest transaction I’ve ever handled. The deal was valued at approximately half a billion dollars, and the first draft of the agreement was only four pages long.

I already knew the client’s directive was to keep things short and move quickly, but four pages is extraordinary for any transaction, especially one of that size. I tried adding what I considered very standard, and relatively light, covenants and protections given the circumstances. The pushback was immediate, not only from the other side but from my own client as well. Eventually, I was given a hard page limit of seven pages. The agreement simply could not exceed seven pages.

There was no real rationale behind that requirement. It was completely arbitrary and unlike anything I had encountered before. But the deal closed successfully, everyone was happy, and in the end it all worked out.

Having been involved in early ICO projects, how has your perspective on token offerings and securities law evolved as regulators have taken a more active stance?

Digital assets are often described as a new financial paradigm rather than an extension of existing systems. Do you believe current securities frameworks are fundamentally incompatible with crypto, or can they be adapted?

I want to answer these two questions together because I think they’re closely connected. I could probably write a short book on this topic, so I’ll do my best to keep it concise.

Early ICO projects were largely launched without a clear understanding of the applicable laws. Many founders simply didn’t realize they were violating securities regulations because the legal landscape was so new. That changed quickly once the SEC began bringing major enforcement actions and making examples of certain projects.

Founders soon realized they needed to be much more thoughtful in how they approached token launches.

I remember early conversations where people genuinely believed ICOs weren’t subject to securities laws, or that issuing a token somehow eliminated the need for a corporate structure. Those assumptions disappeared fairly quickly.

Around 2020, the market began to standardize around offshore token issuance structures. The frameworks that most projects use today became the norm, and while founders initially resisted them because they were expensive and introduced friction, most eventually came to appreciate the legal certainty they provided.

With the Trump administration, however, you began to see sentiment swing back in the opposite direction. Some founders believed they could once again conduct token sales directly in the United States. In my view, that simply isn’t true, and it likely never will be, at least not in the way ICOs were originally envisioned.

Throughout all of these shifts, we’ve seen different administrations and regulators take different approaches to enforcement. At the end of the day, though, the underlying laws have remained largely unchanged.

Even if legislation such as CLARITY or GENIUS becomes law, we won’t suddenly be operating under an entirely new legal framework. The SEC still believes it is the appropriate regulator for companies raising capital. Personally, I’m going to be watching very closely how any proposed transition from SEC oversight to CFTC oversight actually unfolds.

What many people don’t appreciate is that this transition could still impose tremendous costs and friction on founders. They may ultimately find themselves conducting what are effectively miniature securities offerings, complete with many of the same legal expenses and compliance burdens.

So, in many respects, not much has fundamentally changed since 2017 when it comes to token offerings in the United States.

Yes, we’ve seen greater institutional adoption. Yes, we’ve passed stablecoin legislation. But regulators have consistently maintained the same core position. If you’re raising capital, your activities fall within their jurisdiction.

So, are digital assets a genuinely new financial paradigm? In some cases, absolutely.

Bitcoin was, and continues to be, a fundamentally new paradigm because it enables censorship resistant, or arguably censorship proof, value transfer outside the traditional financial system. Ethereum introduced programmable money, which was equally groundbreaking.

Whether those innovations matter to you depends on where you live and how you use them, but they unquestionably represented something new.

Once you move beyond those foundational assets, however, much of what the industry is building today looks more like an extension of the existing financial system than a replacement for it.

The dominant conversations in crypto throughout 2025 and 2026 have centered on stablecoins and tokenized assets. In many cases, we’re talking about U.S. dollars and financial products that have existed for decades, or even centuries, being represented on a blockchain.

That is an evolution of existing markets rather than an entirely new financial paradigm.

When you consider that many tokenized assets will be permissioned, whitelisted, and accessible only to verified institutional investors and high net worth individuals, they begin to resemble today’s financial markets quite closely.

It’s understandable that existing regulators believe their authority extends naturally to these products.

Stablecoins absolutely have the potential to disrupt legacy banking infrastructure and eliminate many inefficiencies if we allow them to. Likewise, putting traditional assets such as stocks and bonds onchain should materially improve the plumbing of the financial system. But that doesn’t necessarily constitute a new financial paradigm.

So I don’t believe existing securities laws are fundamentally incompatible with crypto itself. I do believe they’re fundamentally incompatible with the original crypto ethos. I also don’t believe those frameworks can simply be adapted to preserve that original vision.

What I continue to hope for is that a forward thinking country, likely somewhere in the Global South with a young and growing population, will eventually develop a regulatory framework built specifically for tokens and token based projects.

Such a framework could dramatically lower barriers to participation in financial markets, allowing people to invest in token projects and receive income directly from protocols.

I haven’t yet seen meaningful signs that this will happen, and it may ultimately prove to be unrealistic.

Still, I believe the original promise of crypto, and this is very much a 2018 to 2020 perspective that has become less common today, was the democratization of finance and the removal of unnecessary intermediaries so more people could access financial products and markets.

For that vision to become reality, I believe countries will need to adopt regulatory frameworks designed specifically for crypto rather than forcing crypto into legal structures that were built for something entirely different.

One thing we’ve consistently seen throughout this industry is that founders and lawyers become very good at identifying the most favorable jurisdictions for launching projects. If one country develops a truly workable framework, I believe others will eventually follow.

I also think securities laws are often unfairly demonized within the crypto industry.

At their core, they exist for legitimate reasons. Their purpose has always been to protect investors, the classic idea of protecting “widows and orphans” that emerged after the securities abuses of the railroad era.

So I’m not arguing against regulation, nor am I suggesting there shouldn’t be mechanisms for preventing fraud. Governments will always have a role to play there.

What I am saying is that it simply shouldn’t cost what it costs today to raise capital. The process shouldn’t involve as much friction as it currently does.

The only path I see toward genuine change is allowing companies to raise capital through tokens rather than traditional equity, while enabling those tokens to carry rights such as dividends.

That, to me, would represent a truly new financial paradigm.

Your firm has been active in Web3 since as early as 2016. What were the earliest signals that convinced you blockchain and decentralized finance would become a lasting sector rather than a short-term trend?

Personal conviction in the technology and the ethos. I understood Bitcoin almost immediately. Then I saw Ethereum and what could be built on top of it, and I thought, “Yes, that’s it.”

I became a user, or at least a dabbler, before I became a practitioner. As my practical knowledge grew, my legal knowledge grew alongside it. That legal knowledge exposed me to more applications, protocols, and technology, which in turn expanded my practical understanding even further. It became a personal and professional virtuous flywheel.

Then DeFi Summer happened. That was my personal paradigm shift. That was when I was hooked.

Until this year, when I’ve spent countless hours building software with AI, DeFi Summer was the most time I’d ever spent in front of a computer simply experimenting. I was trying different protocols, losing money, making money, and constantly being impressed by what people were building.

I come from a finance background, and I remember telling anyone who would listen that crypto, and DeFi in particular, was like watching a toddler speedrun the entire history of financial products in an incredibly compressed period of time.

The jump from EtherDelta to Compound to Aave was almost whiplash inducing.

I specifically remember asking, “When are we going to get on-chain options?” A month later, there were already two or three different protocols working on exactly that. On-chain options are incredibly difficult, so I don’t think we’ve fully solved them yet, but the pace of innovation was remarkable.

Soon after that we started seeing structured products, insurance protocols, and increasingly sophisticated financial products.

People sometimes forget that it took hundreds of years for traditional finance to evolve into what it is today.

Crypto compressed much of that evolution into a matter of months.

You advise clients across DeFi, NFTs, and DAOs. Which of these sectors do you believe presents the greatest legal and regulatory challenges over the next few years, and why?

DeFi. The regulators are coming for non-KYC products and projects.

The United States, along with much of the Western world, including traditionally crypto-friendly jurisdictions like the Cayman Islands, the British Virgin Islands, and Panama, have all signed on to something called CARF.

CARF is a non-governmental initiative backed by a transnational organization that will require crypto projects, including DeFi protocols, to report users’ gains to their home tax jurisdictions.

I genuinely don’t know how many DeFi projects are supposed to comply with those requirements. Part of me believes the framework was intentionally designed in a way that makes compliance nearly impossible.

I’m honestly surprised more people aren’t talking about it.

Even setting CARF aside, the world is becoming increasingly difficult for crypto projects, and DeFi is on the front lines. Regulators are going to continue trying to eliminate anonymity, clamp down on anonymous or pseudonymous value transfer, and make examples of founders and companies that don’t conform to those expectations.

I recognize that sounds a little conspiratorial, but I genuinely believe it’s one of the biggest risks facing the industry, and not nearly enough people are taking it seriously.

Our existing financial surveillance system has largely been built around broad anti-terrorism mandates.

There are roughly 12,000 people and entities on the OFAC sanctions list, yet OFAC regulations and the Bank Secrecy Act create friction for billions of ordinary people every single day. They’ve also created an enormous compliance industry of consultants, software providers, and businesses whose sole purpose is helping companies navigate those rules.

That same regulatory apparatus is going to be directed toward DeFi one way or another, and I think it will be extremely difficult for decentralized protocols to shoulder that burden.

If people genuinely care about preserving an open and fair financial system, they should be paying much closer attention to mass financial surveillance generally, and CARF specifically.

I’m not particularly optimistic that they will.

Intellectual property is becoming increasingly complex in the digital asset space, especially with NFTs and tokenized assets. What are the biggest risks founders underestimate when launching Web3 projects?

I actually see the first question a little differently. Intellectual property became a major topic during the original NFT boom, but for the most part those issues have now been worked through. Copyright and trademark laws are real, and founders shouldn’t ignore them. You also can’t copyright AI-generated artwork under current law.

As for the broader question, I think the biggest risks are much more practical.

Founders often run afoul of laws they don’t even realize apply to them. They underestimate how different financial products are from traditional software, and they assume the “move fast and break things” mindset can be applied to financial infrastructure. It generally can’t.

Tax treatment is another area that regularly catches founders by surprise and can create serious financial hardship.

The list of potential legal issues is long, but those are some of the biggest ones.

If you’re building a crypto company, you need a good crypto lawyer. Full stop.

Claude is not your lawyer, and neither is any other AI chatbot. Anything you share with an AI system lacks attorney-client privilege and could ultimately become discoverable in litigation.

Many crypto founders struggle to balance innovation with compliance. What practical advice do you give startups trying to move quickly without exposing themselves to regulatory risk?

This is a difficult question. The traditional tech founder mindset has always been to move fast and break things. In many sectors, that approach is more or less acceptable.

Take Uber as an example. It disrupted transportation, violated local regulations in many jurisdictions, paid fines, and ultimately continued to scale. I’m simplifying the story somewhat, but that has generally been the mindset throughout the technology industry.

You rarely get truly transformative innovation without founders willing to challenge existing rules.

Crypto is different. At their core, many crypto products either are financial instruments, resemble financial instruments, or involve moving and storing value.

That means founders immediately find themselves operating within some of the most heavily regulated areas of modern society, including securities, derivatives, payments, and financial services more broadly.

It’s incredibly easy to make serious mistakes early on, and those mistakes are often permanently recorded on an immutable blockchain.

You can unintentionally create a permanent record of conduct that violates the law without even realizing it. That’s why I try to work with founders as early as possible.

I encourage them to think carefully about every aspect of their business and how it intersects with real-world regulation.

Some of these laws carry severe consequences, and in many cases the statutes of limitation are surprisingly long.

From there, we evaluate which jurisdictions make sense, identify where the underlying activity is legal or unregulated, and build from that foundation.

Ultimately, my job is to slow founders down just enough to recognize that their decisions can have consequences years into the future.

Every architectural decision should be evaluated with legal counsel. That level of caution might seem excessive in other areas of technology, but in crypto it’s essential.

With global regulators taking different approaches to crypto, how important is jurisdictional strategy for digital asset companies today, and how should founders think about it early on?

Our guidance has always been straightforward. Do not issue tokens or operate what I would call “objectionable” crypto projects directly in the United States. I believe choosing the right jurisdiction is one of the most important decisions a founder can make.

Jurisdictional arbitrage is real, and there are countries that are simply better suited for certain crypto businesses than the United States. The list of favorable jurisdictions has been relatively stable since around 2023, but it does change as countries evolve their regulatory approach to digital assets. It’s a moving target.

Timing also matters. There are certain decisions that can’t easily be undone, so I always encourage founders to think through jurisdictional strategy as early as possible.

By “objectionable” crypto projects, I mean the parts of crypto that regulators tend to scrutinize most closely. That includes decentralized exchanges, perpetuals, and projects that involve financial products or financial-like products without KYC requirements.

Those are the businesses where jurisdictional planning is absolutely critical.

Looking ahead, as digital assets continue to reshape finance and ownership, what does the legal landscape look like five years from now, and what role will law firms play in enabling or constraining innovation?

Honestly, it’s difficult to say. I have a hard time imagining that five years from now we’ll be operating under a legal framework that is materially more rational or significantly more favorable than what exists today. At least not if you’re looking at it through the lens of the original crypto ethos.

I think CARF coming into effect will be a significant setback for the industry. My hope remains that a country, likely somewhere in the Global South, adopts a practical, forward-thinking regulatory framework and becomes the jurisdiction of choice for crypto founders around the world.

I think that’s probably the best possible outcome, although I also recognize the chances of it happening are relatively slim.

As for law firms, I don’t think our role fundamentally changes.

Lawyers will continue doing what we’ve always done, helping clients stay out of trouble while building the products they believe can change the world.

Thank you for the great interview. Readers who wish to learn more about legal guidance for Web3 and digital asset companies should visit The Rodman Law Group.