A stay-at-home mom in North Carolina was looking for a flexible way to earn from home. The opportunity seemed simple: get paid to complete online tasks. She earned small amounts at first, enough to build trust in the platform. Then, to unlock higher earnings and access her payouts, she was told to maintain her “membership status” by making deposits, always in crypto.

Small deposits turned into bigger ones. She cashed out her 401(k). She took cash advances on her credit cards. She took a personal loan and by the time she realized the platform was fraudulent, she was out over $110,000.

Then the IRS bill arrived.

Because she had cashed out her retirement to feed the scam, the 401(k) distribution counted as taxable income. She owed regular income tax on it and she owed a 10% early withdrawal penalty on top of that. The IRS does not care that the money was gone by the time the tax was assessed. It cares that she took the distribution.

She came to my team in the worst possible position. She had lost six figures to a scammer. She had a tax bill on the same money the scammer took. And she had nothing left to pay it.

The natural answer is that the scam loss should offset the retirement income, wiping out the tax bill. But the tax code is not clear on whether her situation qualifies. The rules around theft and scam losses sit in a gray area. If her loss does not qualify for a deduction, she owes the IRS for income that no longer exists, with no money to pay it.

She lost six figures to a scammer. And she may still owe the IRS for it.

This is one of the issues I went to Washington last week to push on. (For the broader DC recap, including the CLARITY Act and the new PARITY Act, see last week’s post.)

Why the Tax Code Fails Crypto Scam Victims

The rules around theft losses were written for a different world. They were not built for someone who gets socially engineered into sending crypto to a scammer. They were not built for someone who is impersonated by a fake “Coinbase support” call and tricked into draining their own wallet. I have seen both patterns countless times in my practice this year, with losses ranging from six figures into seven.

The current rules are restrictive and unclear. Whether a given scam qualifies as a deductible theft loss depends on factors most people would never think to evaluate: whether the conduct meets the criminal definition of a ponzi scheme (it probably doesn’t), whether there is a reasonable prospect of recovery, whether the loss was profit-motivated, and a long list of other technical questions.

When the tax code denies a deduction for these losses, the victim gets harmed twice. Once by the scammer. Once by the IRS.

What Reform Looks Like

Fixing this does not require reinventing the wheel. It requires clarifying that crypto scam victims should be treated at least as well as victims of other kinds of fraud. It requires a safe harbor that gives victims and their advisors a clear set of rules: how to document a loss, what counts as a reasonable prospect of recovery, and when the deduction can be taken.

That was a core part of the conversations I had in DC last week, and I came away encouraged. The discussions were detailed, focused on implementation, and bipartisan. That is the right place for a policy proposal to be.

1099-DA Is Going Electronic. That Does Not Fix What Matters.

The other piece of my DC work I want to flag is Form 1099-DA.

Treasury recently requested public comments on the electronic filing of Form 1099-DA. My firm submitted comments, which you can read here. We also plan to testify at the upcoming hearing.

The position I plan to elevate is that moving 1099-DA to electronic filing is fine, it is an improvement at the margins, but the electronic format does not fix the actual problems with the form. As designed, 1099-DA will generate enormous amounts of mismatched and misleading data, and the reporting framework still does not match how people actually use these assets.

What we need is broader reform. And as part of that, we need a crypto voluntary disclosure program. Without one, the millions of taxpayers whose historical records do not line up with what the IRS is about to receive on 1099-DA have no real path to compliance.

The hearing is a chance to get those points on the record. I plan to take it.

Two Issues, One Underlying Problem

Both scam loss relief and 1099-DA reform are about a tax system that needs to keep up with what crypto investors are actually living through. Both are about the difference between a tax code that punishes honest people and one that gives them a fair chance.

I am going to keep working on both.

If you have been affected by a scam, if you have questions about your 1099-DA exposure for the upcoming reporting year, or if you have unreported crypto activity you do not know how to handle, this work affects you directly.

If you want to talk through how any of this applies to your situation, my team is here.

The public conversation on crypto policy has been loud on market structure and quiet on tax. That is changing.

Last week I was in Washington meeting with offices and staff across both parties and both chambers. The conversations have shifted to “how exactly should it work.” And the most ambitious idea we have been speaking about for years, a crypto voluntary disclosure program, just made it into legislative text for the first time.

Inside the Meetings

Over a few days I met with Ways and Means staff on both sides of the aisle, Senate Finance staff on both sides, the Taxpayer Advocate’s office, and the staff of Representative Steven Horsford, who just introduced a major piece of digital asset tax legislation. (More on that below.)

The focus of these meetings was the details. How a crypto voluntary disclosure program (VDP) would actually work, what guardrails it needs, and what the scope of a scam loss deduction should look like. Who qualifies, and how.

These conversations mean the policy work we have been discussing for the last couple of years is getting real traction.

And the interest is bipartisan. These are not partisan issues. Honest taxpayers who want to come into compliance or are victims of scams are from all parties.

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CLARITY Moved, and Why That Matters for Tax

While I was in DC, the Senate Banking Committee reported the Digital Asset Market Clarity Act out of committee by a vote of 15-9. Two Democrats voted with every Republican to advance the bill.

A simple way to think about CLARITY: it is the market structure bill. It would establish the broad federal regulatory framework for digital assets and give the industry the framework it has been asking for.

CLARITY is not a tax bill. But it matters for tax. Many members of the tax-writing committees have said they want the regulatory framework in place before they take up how to tax these assets. Banking and Finance have significant overlap, with several senators sitting on both. The same people are getting educated on digital assets from two angles at once.

Whether CLARITY clears the floor this year is uncertain. The legislative calendar before the elections is tight, and the timing of digital asset tax legislation is uncertain. But the behind-the-scenes work has not stopped. It is happening. It is just not always visible.

A Crypto VDP Just Made It Into a Bill

Last week, Representative Steven Horsford introduced the PARITY Act. At a high level, the bill addresses several digital asset tax pain points and moves crypto reporting closer to how other asset classes are treated.

The PARITY Act is the first piece of legislative text that includes language for a crypto voluntary disclosure program.

That is a milestone. For years, the crypto VDP has been a policy idea, the subject of meetings, memos, comment letters, and op-eds. Now it is text in a bill that has been formally introduced.

Why does it matter? Most of the crypto tax non-compliance I see in my practice is not coming from bad actors. It is coming from people who did not understand the rules. From people whose records were never going to be reconciled by any retail crypto tax software. From people who got scared off filing by the threat of penalties and audits on activity going back five or ten years.

Take a father and son I work with who own a winery in Iowa. They started investing in crypto in 2017 as a side project on centralized exchanges. They did not know most of their crypto-to-crypto swaps were taxable. Six years later, they have never reported any of it. The unreported gains are significant.

They want to be compliant. But the prospect of reconstructing six years of activity and walking into a potential audit with that kind of exposure is terrifying. So they have not filed. The IRS does not get paid. They do not get to move on.

A VDP changes that calculus. It gives people in their position a clear path to come forward, certify non-willfulness, and pay what they owe without crippling penalties. There are tens of thousands of taxpayers (or more) in the same position. A VDP gives them a path home. It also raises revenue for Treasury. It is one of the rare ideas in tax policy that is both pro-taxpayer and revenue-positive.

Where This Goes From Here

Crypto tax is happening. Just not loudly. The work is bipartisan, it is moving, and it is now about the how, not the whether.

The PARITY Act is a meaningful step, and a VDP in legislative text is a first.

CLARITY is the gating item. If it moves, tax follows. If it stalls,the groundwork is being laid either way.

Next week I will write about the other half of what I worked on in DC: the case for a scam loss deduction and why Treasury’s electronic 1099-DA proposal does not fix the problems that matter. Subscribe so you do not miss it.

If any of this applies to your situation, send me a message.

We just wrapped up Bitcoin 2026, the largest crypto conference in the world, and I wanted to bring you inside it. I spoke on crypto tax reporting, including the new Form 1099-DA. We had several extremely productive meetings with policymakers, including Senator Cynthia Lummis, Senator Bernie Moreno, Representative Nick Begich, and Patrick Witt. We hosted a happy hour at The Venetian that pulled in more than a hundred people to talk policy, taxes, and what’s actually at stake for crypto right now.

The short video below captures those three days in about three minutes.

Why I Keep Showing Up

If you’ve been following along, you’ve seen me write about The Idea That Changed the Room, where I laid out a crypto voluntary disclosure program (VDP) and the traction it’s been picking up in DC. Vegas was continued proof that the conversation is no longer one-sided.

Investors are nervous about Form 1099-DA. Builders are quietly weighing whether to stay in the United States. And policymakers are asking us for input instead of just sending audits. The window to make the tax rules actually fit crypto, instead of being shaped to kill it, is open right now. That’s what I’m fighting for, and it’s why these three days mattered.

Subscribe below to follow the policy work as it develops. More coming soon.

Next week I’ll be at Bitcoin 2026 in Las Vegas, the largest gathering of the year for the Bitcoin and broader crypto community. From April 27 to 29, The Venetian will be filled with everyday crypto investors, founders, developers, miners, and, just as importantly, the policymakers shaping where this industry goes next.

I’ve attended this conference several times, and last year I spoke on crypto tax. This year, policy conversations are front and center. The conference even includes a “Code & Country” industry day built around exactly that intersection, where technology and Washington meet.

Here’s what I’ll be doing there, and why it matters for you.

Speaking Tuesday: Taxes 1099-DA: What You Need to Know

On Tuesday, I’ll be speaking on “Taxes 1099-DA: What You Need to Know.” The new 1099-DA reporting regime is one of the most consequential changes crypto investors and builders have faced in years, and most people in the industry still do not know what is coming, how it will land on their tax returns, or where the pressure points are.

Meetings with Legislators and Policymakers

Alongside the stage sessions, I’ll be in one on one and small group meetings with legislators and policymakers who are actively shaping crypto tax and regulatory policy.

On my last trip to DC, a crypto voluntary disclosure program was the idea that got every office leaning forward, because it would give millions of everyday crypto holders a real path back into compliance and, unlike most reform proposals, it is revenue positive. That is the kind of traction you only get from showing up trip after trip, bringing real client stories, and refining the ideas until they are ready. Vegas is the next stop on that trail. Conversations that started as “tell us about your concerns” have turned into “send us draft language,” and I plan to keep that going.

Join us For a Happy Hour about Policy and Progress

We’re also hosting a happy hour during the conference titled “Crypto Needs a Voice: Policy, Progress, and Participation.” I’ll kick things off with brief remarks on what’s happening in Congress right now, what we’re hearing behind the scenes, and what the industry should be watching in 2026. After that, it’s what Vegas does best: real conversations, real connections, and an open bar.

If you’re attending Bitcoin 2026 and want to join us, reach out and we’ll share the details.

Bring Your Story to Vegas

Every meeting I take in DC, and every panel I participate in, is stronger when it is grounded in real stories from real taxpayers and builders. If you have faced unfair tax treatment, confusing 1099-DA guidance, or a compliance situation that does not square with how this technology actually works, I want to hear about it. Those stories shape what I bring into closed-door meetings.

Subscribe to stay up to date, including what I heard from policymakers and what it means for the year ahead.

Together, we can make sure the next chapter of crypto tax policy is written with builders, investors, and everyday users in mind.

Today is Tax Day. Across the country, millions of Americans are filing their returns, chasing down records, and making sure they got it right. It is the one day a year when tax policy stops being something that happens in Washington and becomes something every family feels at the kitchen table. For crypto holders, that feeling can be especially heavy.

Tax Day is a reminder that taxes are not an abstract policy debate. They are personal. They hit your bank account, your peace of mind, and your willingness to keep building and investing in this country. When the rules are clear, people comply and move on with their lives. When the rules are broken, people get stuck, and that is where too many crypto holders are right now.

That is what we are fighting for. Rules that make sense for the technology people are actually using. A clear path for honest taxpayers to get right with the IRS. Fair treatment for the millions of Americans who bought, sold, staked, or swapped crypto and are now trying to figure out what they owe.

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I have spent the past year walking into rooms in Washington and sitting across from the people who write these rules, carrying your stories with me. Those stories are working. Lawmakers are listening. The conversations are getting more specific, and the asks we are getting back are more concrete than ever.

If you filed today, I hope it went smoothly. If it did not, you are not alone, and that is exactly why this work matters.

Thank you for following along, for sharing your stories, and for showing up. We are just getting started.

Last week I was back in Washington. If you have been following along, you know the rhythm by now. Show up, bring real examples, sit across the table from the people writing the rules, and do the work of turning ideas into language. In our last update, I wrote about how conversations were moving from ideas to drafting. This trip took that a step further. One idea kept landing harder than anything else I brought into the room: a crypto voluntary disclosure program.

I have been talking about a VDP for months. In prior meetings, I raised the concept alongside other priorities, wash sales, de minimis, cost basis. People were interested, and the idea always landed well. But this trip it really got attention

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Why a VDP, and why now

Let me back up for anyone new here. Right now there are millions of Americans who hold or have traded crypto and have tax issues they do not know how to fix. Some missed reporting in years when guidance barely existed. Some have incomplete records because exchanges shut down or because DeFi activity does not produce a 1099. Some just did not know what they were supposed to do.

These are regular people who got into crypto early, made trades on platforms that did not send tax forms, and now feel stuck. I see this every day in my practice, and I have written about why taxes are the real fight for crypto, because when the rules are confusing or punitive, people stop trying to comply. The fear of stepping forward is real. People do not know what will happen, how far back the IRS will look, or how much it will cost. So they freeze.

A voluntary disclosure program gives those people a clear path back into compliance. You know the penalties up front. You know how far back they are going to look. The process rewards good faith instead of punishing it. The IRS gets revenue it is not currently collecting, and taxpayers get certainty they cannot currently find. That is a deal that works for everyone.

I have been making this case in DC since last year. This trip, the case started making itself.

What I heard across the board

I had meetings across both chambers last week, with Senate offices, House staff working on active legislation, and people close to the drafting process. A few things came through clearly no matter which room I was in.

First, crypto taxes are the next priority after market structure clarity is done. That was consistent everywhere and the interest is real, not hypothetical. The message I kept hearing was that we need to move fast while the attention is here. That means having proposals and language ready so we are not scrambling when the opportunity comes.

Second, Treasury can do some of this without waiting for Congress. More than one person told me that many of the changes we are pushing for are within the Treasury’s authority. That opens a second lane. Legislation is one path. Treasury guidance is another. We are pursuing both.

Third, and this is the one that surprised me, every office I walked into had a stronger reaction to the VDP than to anything else I raised. Wash sales, cost basis, de minimis - those are important and I will keep pushing on all of them. But the VDP was what got people leaning forward.

The moment it clicked

One of the Senate meetings was extremely fast paced. I talked about what I see on the ground, the current audit climate and the confusion among everyday taxpayers. I shared the same kinds of stories that our clients brought to Capitol Hill last fall. We talked about ways the IRS or Treasury provide some solutions.

Then I brought up the VDP.

The Senator’s whole demeanor shifted. Clarity is considered revenue neutral, but a crypto VDP could be revenue positive. That is a political win on top of a policy win. The Senator was excited to talk in detail about it.

Building the network

Beyond the VDP, the week produced something else that matters: new connections and deepening relationships. I got an offer to be introduced to IRS leadership. I was offered introductions to counterparts in offices I have not been able to reach yet. And I had a detailed walkthrough of the PARITY Act with the team that is drafting it, which is further along than most people realize.

None of that happens on a first visit. It happens because we have been doing this consistently, trip after trip, follow up after follow up, going back to our first meetings with Capitol Hill tax staffers and our meetings with Treasury officials. When staffers pull out notes from your last meeting before you sit down, that shows that our work is compounding.

Where this is going

In earlier posts I wrote about building relationships, earning trust, and developing ideas that are ready when the window opens. The VDP started as one item in a list of priorities. It is now getting traction. That did not happen by accident. It happened because we kept showing up and kept refining the idea.

I am preparing the materials that offices asked for. Several offices are independently moving in the same direction on this, and I am making sure they know what the others are doing.

A VDP can move through legislation or through the Treasury. It could attach to clarity, to the PARITY Act, or come through as an administrative action. I do not know yet which path gets there first. But the destination is the same: a real way for crypto taxpayers to get right with the IRS.

Every trip to DC builds on the last. The conversations get more specific, and the asks get more concrete. “Send us draft language” is a very different conversation than “tell us about your concerns.”

I will be at the Bitcoin conference soon and will continue these conversations in person. If you have been following this journey since ETHDenver or since the Senate hearing, you know this work is cumulative. If you have a crypto tax story, especially if you are someone who wants to comply but does not know how, send it my way. Those stories are the most effective tool I bring into any room in Washington.

Thanks for following along. More soon.

This video is a quick cut of that energy. You’ll see clips from my remarks, mixed with real reactions from attendees about what’s working, what’s broken, and what needs to change. A few lines from the night stuck with me: trying to force something modern into a framework built in the 1930s doesn’t make sense. People want to build in the U.S., but there still isn’t enough clarity to do it confidently. And the conversation in DC has shifted from “why crypto” to “how do we legislate to protect it and keep it in the United States.”

That shift is real. And it’s happening because everyday investors and builders are finally being heard. Watch the reel, and if it resonates, share it with one person who cares about crypto’s future here. If you have a crypto tax story, send it my way. The most effective advocacy always starts with real examples.

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If you want behind-the-scenes updates from DC and plain-English breakdowns of what’s coming next, subscribe here.

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In our last update, I closed with “where we go from here,” and the answer was to keep showing up, keep bringing real examples, and keep doing the work that turns our goals into workable language. Last week in Washington was the next step in that arc.

I had a full schedule of substantive meetings across both chambers, with the committee teams that write the first drafts and the senior leadership offices that decide what gets priority when time gets tight. These were working sessions, not introductions.

Washington has a lot of meetings, and most of them blur together. People rotate in and out, talking points get recycled, and the easiest thing in the world is to leave a room feeling like “progress was made” without anything actually moving.

Last week did not feel like that. In meeting after meeting, it was clear we were not starting from zero. Staffers knew my name, remembered what we sent, and recognized us as a reliable resource. Instead of spending time on surface-level education, I spent our time where it matters: the technical details that determine whether crypto tax reform will actually help everyday Americans comply, or whether it will accidentally create another layer of confusion and risk.

That is the shift we have been working toward. In Washington, trust is earned. Last week was another step toward being seen as practical advisors who are willing to do the hard work of making policy real.

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Where things stand: timelines, themes, and the Main Street test

Market structure is the immediate priority, and crypto tax is next. The interest in crypto tax legislation is real. Staff and policymakers are already thinking about what a package could look like, how it could move, and what needs to be ready when the window opens.

I also heard a practical political reality: timelines can compress fast. That means the period for shaping language can open quickly and close just as quickly. That is why I keep doing this in a disciplined way. The work is not “one trip”, but building a record of credibility, plus having ideas and language that is ready when it matters.

Two examples of in-depth conversations

1) A Crypto Voluntary Disclosure Program

One of our core goals was to emphasize the need and “win-win” of a crypto voluntary disclosure program: a structured, predictable path for non-willful taxpayers to get right with the IRS.

The encouraging part was not just that people listened. It was how they engaged. The discussion went straight to the elements that determine whether an idea can become real policy: how to structure a predictable penalty framework, what “fair” looks like in practice, how to design incentives that actually drive participation, and how to scope a program in a way that is defensible.

I emphasized what I see every day. There is a large population of taxpayers who want to comply, but they are stuck. Records are incomplete. Activity spans years. People fear stepping forward because they expect an open-ended process with unpredictable consequences. A well-designed program flips that dynamic by rewarding good faith and giving people a realistic off-ramp back into compliance.

I also discussed something important. To move an idea like this, it needs more than anecdotes. It needs credible estimates and a clean framework that makes it easy for policymakers to understand what it achieves and why it is administrable.

That is exactly where we can contribute.

2) Wash sale rules that fit crypto

Wash sale treatment for digital assets is an area that will impact nearly every crypto investor, and the drafting choices here will determine whether the rule becomes enforceable or chaotic.

Our point was simple: if the legal standard is subjective, everyday taxpayers pay the price. In traditional markets, “substantially identical” has a narrower set of instruments and a longer history. In crypto, it becomes a trap. There are a variety of wrappers, bridged assets, staking derivatives, and exposure products that look similar but are not actually identical.

I discussed what “objective” could mean in crypto: definitional clarity, identifiable characteristics, and approaches that reduce guesswork for both taxpayers and the IRS. The point is not to create loopholes. The point is to create rules that can be followed without turning compliance into the need to hire a tax attorney.

That is what protects everyday investors.

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This week: ETH Denver

This week we are going to ETH Denver, and we are hosting an event for investors and builders.

The goal is to bring this conversation back to the community. I will share what we learned in D.C., what momentum looks like behind the scenes, and why the details matter. Crypto legislation cannot be a Washington-only conversation. The people most affected by these rules are the people building, investing, transacting, and trying to comply in real life.

ETH Denver is also a chance to keep collecting real stories and real fact patterns, then translating them into language that policymakers can actually use.

Where this chapter leaves us

This work is becoming cumulative and each trip builds on the last. Each set of follow-ups makes the next meeting more substantive. And each set of real examples makes it harder for lawmakers to write rules that look clean on paper but fail in practice.

That is the mission: keep Main Street in the room while the rules are being drafted, and keep bringing the kind of clarity that makes compliance feel normal again.

Last week felt different. In our “we are going to DC next week” post, we set a simple plan. Meet lawmakers, share real stories, and push for practical crypto tax fixes. We did that and more. We said we would show up, and we showed up with a stronger voice than ever.

Crypto taxes are the most important fight because they touch everything. If the rules are confusing or punitive, builders leave, investors pause, and everyday payments stall. When the rules are clear and fair, compliance goes up and innovation stays in the US. I wrote about the need to prioritize crypto taxes and why it unlocks every other policy goal.

I am not a career political insider. I am a taxpayer, an attorney, and a dad who believes democracy works when regular people sit across the table from the people who write the rules. Last week proved that. People in DC are listening. They asked questions. They took notes. They asked for our suggestions. That only happened because you stepped forward, contributed your stories, and came with us. Thank you.

Why this trip was different

A year ago we were explaining what crypto is and why it matters for American competitiveness. We hosted a private dinner in Nashville where fifteen clients spoke directly to Senator Blackburn about how taxes block everyday use. We met lawmakers in DC earlier this year to map a path forward. We kept publishing real audit stories, and I met with Treasury officials to comment on GENIUS and dollar-stable payments.

This time we returned with ten clients and a year of groundwork. We brought lived experience to the table. We translated it into sensible fixes. And we heard something new in response. Bring us language. Bring us examples. Help us get this right.

Highlights from meetings on both sides of the Capitol

We had a jam packed week, including seven meetings across both chambers. Senate Finance, House Ways and Means, the Majority Whip, and the Finance Chairman. We met in committee rooms and inside the Capitol. These meetings happened because of relationships we have been nurturing all year, and each conversation moved the ball forward.

The message was clear in every room. Crypto taxes are broken. They need to be fair, workable, and written for real people. Not just the largest platforms. Not just the simplest transactions. People who want to comply should be able to comply.

Meeting the Majority Whip

Kicking off the week, we met with Majority Whip Tom Emmer at the Capitol. The meeting happened because of a relationship we have built over time. It started with a dinner in Chicago where we swapped stories and set a shared goal. Keep crypto tax practical and front of mind. We followed up with notes, case studies, and clear examples that his team could use in real conversations. That steady cadence mattered and when the calendar got tight, the door still opened.

Amid a live shutdown fight, we cleared security at the Capitol and sat down with Whip Emmer and two of our clients. With DC deep in a government shutdown, the political climate was tense, but the Whip made time. We discussed that crypto tax is a priority, not a side topic. Our clients explained how uncertainty pushes activity offshore and how a normal weekend of crypto trading can create a tax footprint that software cannot cleanly report. He asked focused questions, pushed for specifics, and came back to the same point. Policy clarity is moving. Taxes need to move first. We left with a commitment to keep sending real cases so his office can help turn stories into statute.

Ready to join a future Hill meeting? Message me!

Ways and Means staff, then and now

A few months ago I met with Ways and Means staff and wrote about it. We talked about policy principles and the need for clear rules that fit how crypto actually works. This time we brought even more strength - clients to share their specific fact patterns. That changed the discussion in two ways.

First, we walked through areas that had not gotten much attention so far, but impacted many of our clients. For areas such as liquidity pools and wrapped tokens, staffers have heard of these, but seeing a step-by-step example matters. We shared a cleaner path.

Second, we put new suggestions on the table. Most investors we meet want to get right with the IRS but do not know how to rebuild records or fear open-ended lookbacks. We need a compliance path with a limited lookback, predictable penalties for non-willful cases, and a good faith basis reconstruction safe harbor would raise compliance and reduce fear. The staff heard that and asked for more information. That is a gap we can help fill.

Senator Blackburn and a year of relationship building

The meeting with Sen Blackburn’s staff came from a foundation started last year with a dinner in Nashville. Fifteen clients around a table sharing with a United States senator why crypto matters to families and small businesses. It continued at the Bitcoin conference in Las Vegas, where we sat down for lunch with Sens Blackburn and Lummis and compared notes on tax timing for staking and mining. It kept moving in DC earlier this year, when we walked offices through de minimis, wash sales, and cost basis issues.

Last week, with Senator Blackburn’s staff, we brought it all together. We shared stories and potential fixes. They asked smart, detailed questions. We discussed policy areas that matter to you. They asked us to keep the suggestions flowing and to continue to coordinate with them so language is ready when the Finance Committee marks up a bill. We are part of the process because we built trust the right way. One conversation at a time.

Inside Our Lunch with the Finance Chair

Our small-group lunch with Chairman Mike Crapo was a highlight of the trip. He leads the Senate Finance Committee, where any crypto tax bill will be written. He told us plainly that he wants to understand crypto, that he wants clear rules of the road, and that he wants to get it right. Then he listened.

What moved the room were the client stories. People who tried to comply and ended up in audits that made them feel like criminals for using modern tools. People who paused investing or moved activity abroad because the current rules do not match the technology. The Chairman asked for short, surgical adjustments tied to real fact patterns. Show us how to avoid taxing simple transactions. Show us how to give honest taxpayers a path back in. We left with optimism for crypto taxes and a new relationship.

Senate Finance Majority staff

This meeting built on our September visit that I wrote about. Back then we aligned on high level goals and the need for rules that reflect how crypto works day to day. This time we came back with client stories and practical fixes. Staff focused on what will move a bill forward and how to translate lived examples into clear definitions, simple reporting steps, and guidance that can be applied by investors without guesswork.

The conversation centered on outcomes. Make compliance easier for honest taxpayers. Keep the system neutral across different ways people hold and use digital assets. Preserve U.S. competitiveness so activity stays here. The tone was collaborative and results driven. We made clear that our team will remain a standing resource as crypto tax moves through committee.

Where we go from here

Our goal is simple. Make sure Main Street is heard as Congress drafts crypto tax legislation. We are now drafting and sending the follow ups each office requested. Based on what we heard, a crypto tax package could move to markup in the coming months so we need to continue to engage with lawmakers.

This entire week was the culmination of a year of planning. Private dinners. Roundtables. Comment letters. Case studies. Client voices. It worked. As we head into next year, we will formalize the schedule. Regular advocacy trips. Public drafts for feedback. Clear timelines. We will share dates and ways to participate soon so you can plan ahead for 2026.

If you want to help, add your voice. Share your fact patterns. Subscribe for the deep dives. Bring a friend to the next roundtable. Democracy only works when people show up. Last week, you showed up. DC listened.

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Crypto taxes touch everyone

Whether you are an investor, a dev, a miner, a startup CFO, or just the person who used USDC to pay a contractor, crypto taxes touch every corner of activity. If America is going to be the crypto capital of the world, we have to fix the rules that make ordinary use expensive, confusing, and risky.

Over the last year, our mission has been simple: bring real people’s stories to Washington. We’ve sat with lawmakers and staff to explain, in plain English, what’s broken and how to fix it. Next week is the biggest step yet.

Where we’ve been (and how it set the stage)

A quick look at the key moments from the past year that made next week possible:

• Nov 22, 2024 — Nashville: Private dinner with Sen. Blackburn; 15 clients shared on-the-ground challenges.

• Feb 12, 2025 — Washington, D.C.: Crypto roundtable with Sens. Blackburn, Lummis, Moreno, Scott, and Hagerty; 20 clients in the room.

• May 27, 2025 — Bitcoin Conference: Joint lunch with Sens. Blackburn and Lummis; 10–15 clients briefed both senators on tax pain points.

• Jul 25, 2025 — Chicago: Dinner with House Majority Whip Tom Emmer focused on crypto tax changes.

• Jul 29, 2025 — Capitol Hill: Meetings with Sens. Lummis & Blackburn and Treasury officials to align legislative and administrative paths.

• Aug 29, 2025 — Chicago: Policy dinner with Don Trump Jr. and Illinois business leaders to elevate crypto-tax priorities.

• Sep 3, 2025 — Capitol Hill: Staff meetings with Senate Finance (majority & minority) and House Ways & Means on our action points.

• Sep 11, 2025 — Chicago: Private dinner with Whip Emmer; momentum check heading into fall.

• Sep 15, 2025 — Chicago: SEC Commissioner Hester Peirce fireside chat + private lunch with builders (including our clients).

• Next week (Nov 5–6, 2025): Private lunch with Senate Finance Chairman Mike Crapo, then a full day of Capitol Hill meetings with Senate and House tax staff.

Why now is the moment

For the first time, Washington is treating crypto as core financial infrastructure and moving accordingly. This summer, Congress passed and the President signed the GENIUS Act, the first federal digital-asset law creating a national framework for payment stablecoins. That’s not just symbolism; it’s proof lawmakers can deliver bipartisan outcomes in this space.

With stablecoin groundwork in place, tax clarity is next. The Senate Finance Committee just held a dedicated hearing on October 1 titled “Examining the Taxation of Digital Assets,” where members pressed witnesses on staking, mining, 1099-DA, and everyday transactions. When the tax-writing committee is workshopping specifics in public, it’s a signal: policy is moving from debate to drafting.

Sen. Cynthia Lummis has put a comprehensive digital-asset tax bill on the table, including a $300 de minimis for small personal transactions (with a $5,000 annual cap), timing relief for mining and staking, and a modernization of other code sections under discussion. The bill is being actively socialized, and there’s chatter that a markup could come in the months ahead. The exact timing always shifts on the Hill, but the legislative machinery is clearly engaged.

What’s the opportunity next week?

Because of the relationships we’ve built and the stories we’ve shared, we are meeting next Wednesday, Nov 5 with Senator Mike Crapo, the Chairman of Senate Finance - the Senate committee that writes the tax code. In practice, that means:

• The Chairman has significant influence over the version of any crypto-tax bill that leaves committee.

• He can shape what makes it in, what gets refined, and what doesn’t advance.

• If you care about U.S. crypto policy, this is the table that matters and this is the time that matters.

We are bringing twelve clients whose stories mirror thousands more: miners taxed before cashing out; builders trapped by ambiguous reporting; long-time users hit with erroneous 1099s; founders airdropped tokens they never sold but still got “income.” The next day (Nov 6), we’ll be on Capitol Hill in small, topic-driven meetings with Senate Finance and House Ways & Means staff, the people who brief members and often craft the actual lines of the statute.

What we’re taking to the table (our policy points)

These are some of the changes we believe unlock real utility, cut red tape, and keep innovation here:

1) Treat payment stablecoins like cash equivalents

Goal: When used for payments, stablecoins shouldn’t trigger gains/losses.
Fix: Remove reporting requirements for stablecoins when used in payment transactions.
Why it matters: No one can “spend digital dollars” if buying coffee means tracking capital gains.

2) End phantom income for staking and mining

Goal: Stop taxing block rewards twice - when received and when there’s a sale.
Fix: Recognize income at disposition, aligning tax with cash flow.
Why it matters: Builders shouldn’t owe taxes on assets they haven’t sold and may not be able to liquidate.

Reply with your top priority (1–2 lines). We’ll weight these in our leave-behind.

3) Airdrops and unsolicited tokens: tax on sale, not receipt

Goal: Don’t tax people on assets they didn’t ask for and can’t readily monetize.
Fix: Establish that value is recognized at sale/exchange, with clean basis & holding-period rules.
Why it matters: Prevents surprise tax bills and audit nightmares for ordinary users.

4) Keep “wash sale” rules out of digital assets

Goal: Avoid importing a 1930s stock rule into a 24/7 crypto market.
Problem: Crypto reporting is already too complex. A blanket 30-day “substantially identical” regime would explode Form 8949 line items, collide with the new 1099-DA rollout, and penalize normal behavior (rapid re-entries after sharp moves, wallet hygiene, bridging, LP rebalancing). Thirty days in securities is not thirty days in crypto.
Fix: Codify that digital assets are not subject to §1091.

5) Create a voluntary disclosure path for past years

Goal: Give taxpayers a clear, fair way to reconcile prior crypto activity without crushing penalties.
Fix: Establish a crypto-specific streamlined compliance program (modeled on FATCA/FBAR streamlining) that lets taxpayers certify non-willfulness, amend returns, and pay reduced penalties to come into compliance.
Why it matters: Millions want to get right with the IRS but lack a path; a tailored program would unlock real revenue, cleaner data, and wider compliance.

How you can help (right now)

• Share your story. If you’ve been hit by any of the issues above, tell us. Specifics help us draft better fixes.

• Subscribe and forward this post. We’ll publish a full debrief after our time in D.C., including what’s moving and why it matters.

• Bring a friend into the conversation. More voices = better policy.

We’re outsiders. But we’ve earned our seat at the table by showing up with real cases, real data, and real solutions. Next week, we’re sitting down with the most important person in the room at the most important time—and the very next day we’ll be with the staff who move ideas into law.

Let’s make the U.S. the best place in the world to build and use crypto by fixing crypto taxes the right way.

— Andrew Gordon, CPA + Attorney

P.S. Nothing in this post is legal or tax advice. For personal advice, contact a qualified professional.

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David Fields has lived at the intersection of media, technology, and incentives for more than a decade, first in investments and M&A at Disney (including work on the Pixar deal), then as head of investments for Michael Eisner, and today as co-founder of ReadyAI, a company building on the frontier of AI × crypto.

Over the past year, David has joined our small-group meetings with senators and policy staff, participated in roundtables in Washington and Las Vegas, and most recently sat down for a working lunch with SEC Commissioner Hester Peirce.

“From afar, D.C. felt like a black box. In the room, you realize there’s a real willingness to prioritize crypto—if we show up with specifics.”

From Disney to ReadyAI

An economics background and an early thesis on incentives pulled Fields toward Bitcoin in the early 2010s. Ethereum followed, and so did a conviction that AI and crypto would converge.

With his co-founders he launched ReadyAI to attack a fundamental bottleneck in AI: turning messy, unstructured data into high-quality, structured inputs that models can actually use.

Mission (today): “Structure all the world’s information for AI, so companies and individuals can build reliable applications.”

How they’re doing it: ReadyAI operates a subnet on Bittensor that coordinates a decentralized network of participants who complete and score tasks. Rewards flow to miners, validators, and the subnet over time via a fair-launch token model.

“Incentive design matters. If miners can game the system, you don’t get the output you want. Getting that alignment right is one of the hardest parts.”

Why Bittensor—and why incentives are the point

Decentralized AI is a design choice for ReadyAI. On Bittensor, the rules are visible, the software is open, and contributors respond to incentives. That openness is powerful and unforgiving.

Fields calls the early days of launching a subnet “a back-and-forth in development” where you test, tighten, and re-test to ensure high-quality structured data wins out over clever exploits.

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Inside lunch with SEC Commissioner Hester Peirce

Fields joined a small builders’ lunch during Commissioner Peirce’s recent visit to Chicago, focused on nuts-and-bolts questions:

• Market structure & token issuance: What does a workable path look like for teams launching and sustaining a network?

• Safe harbor concepts: Could a time-boxed framework allow projects to decentralize before full securities compliance applies?

• Fair-launch models: How do no-pre-sale, no-treasury distributions (like Bittensor subnets) fit under existing interpretations?

“She was candid and engaged, clear that the goal isn’t a free pass, but fair guidelines people can actually follow in the U.S.”

Fields’s takeaway: progress requires both Congressional clarity and regulatory guidance. We’re still early.

If he had the policy pen for a day

Two priorities rose to the top:

1. Crystallize a Safe Harbor so good-faith projects can launch, iterate, and decentralize with clear expectations.

2. Clarify token buybacks - now common in crypto but under-defined in current rules - so teams know what’s permissible.

In the rooms where policy gets personal

Fields attended our D.C. meeting and our Las Vegas lunch (with a ~15-person table discussion with Sens. Lummis and Blackburn).

• D.C.: “A breath of fresh air after a hostile period. The openness to hear specifics from builders felt real.”

• Vegas: Tight-knit, policy-dense, and—importantly—post-bill momentum with a sober view of what’s still ahead on market structure.

“Seeing senators prioritize crypto up close was energizing. Night-and-day difference from the perception you get watching from California.”

Why he’s optimistic

• Crypto has gone mainstream. Ignoring it is no longer an option for Washington.

• Policy conversations are evolving. Lawmakers want operational detail—exactly what founders and investors can provide.

• The community is growing up. Small rooms, clear asks, and real examples are replacing slogans and hype.

“We’re at a turning point. If the people building the future don’t speak up, someone else will define it for them.”

Editor’s note

David has also been collaborating with our team between events, including prep calls, drafts, and feedback loops that translate builder realities into actionable policy asks. That homework is making our meetings sharper.

How builders and investors can get involved

If you believe in fair, clear, and workable crypto policy, here’s how to participate:

1. Subscribe to get on-the-ground updates from Washington about the future of crypto policy and how each decision affects Main Street investors, builders, and taxpayers.

2. Share your story. Audit issues, staking or mining challenges, confusing tax forms—real examples help policymakers see what needs fixing.

3. Join us. Our next webinar is October 23 (2:00–3:00 p.m. CT). David will join at 2:30 p.m. CT to talk about the safe harbor concept and lessons from the Peirce lunch.

Last week, the Senate Finance Committee, chaired by Senator Mike Crapo, held a hearing titled “Examining the Taxation of Digital Assets.”
It was one of the most serious and thoughtful discussions we have seen in Washington on crypto taxation. For years, policymakers have debated crypto in the context of speculation, fraud, or market volatility. This time, they finally focused on the actual tax rules that affect millions of Americans who own or build in crypto.

As someone who has spent the last decade in the trenches helping clients navigate crypto audits, compliance investigations, and complex reporting, I was encouraged by the progress but also reminded how far we have to go.

1️⃣ What the Hearing Covered

The hearing featured four expert witnesses who represented the full spectrum of perspectives:

• Jason Somensatto (Coin Center) explained how the IRS’s decision to treat crypto as property creates taxable events for even the simplest activities, such as buying a cup of coffee.

• Andrea Kramer (ASKramer Law) argued that the tax code is flexible enough to accommodate digital assets but needs clarity. She urged Congress to define what counts as a “commodity,” what it means for an asset to be “actively traded,” and to enact a de minimis exemption similar to the $200 foreign currency exception.

• Lawrence Zlatkin (Coinbase) called for parity with traditional finance. He pointed out that lending stock or bonds is tax free, while digital asset lending could trigger a taxable sale. He proposed several priorities, including extending tax-free treatment to digital loans, safe harbors for staking and lending, and consistency in partnership and ETF rules.

• Annette Nellen (AICPA) emphasized administrative simplicity. She recommended extending mark-to-market to digital asset dealers, clarifying section 864 safe harbors, and fixing the qualified appraisal rules for donated digital assets.

Over two hours, senators raised several key issues affecting the crypto ecosystem:

1. De minimis transactions – how to handle small everyday purchases.

2. Staking and mining taxation – when rewards should be taxed.

3. Broker reporting and privacy.

4. Qualified appraisals for donations.

5. Foreign investor rules and safe harbors.

6. Section 6050I and the $10,000 reporting rule.

7. The broader crypto tax gap and enforcement.

It was encouraging to see so many senators engaged. But it was also clear that, while the questions were sophisticated, more real world solutions need to be offered.

2️⃣ The De Minimis Debate: Missing the Real Problem

Chairman Crapo and Senator Wyden both pressed the witnesses on how a de minimis exemption would work. Could it be abused? Should there be income or transaction caps?

Those are fair questions, but they miss the main point. The real issue is not Bitcoin purchases for coffee. The real problem is that stablecoins are being treated as property rather than as cash equivalents.

Every time someone uses a $1 stablecoin to buy a $1 item, the IRS expects a gain or loss calculation. That is impractical, unnecessary, and entirely disconnected from how digital payments actually function.

If Congress wants to make small-transaction relief meaningful, it needs to exclude stablecoins from capital gains reporting altogether. No one will use digital dollars for payments if it triggers hundreds of taxable events every month. Fixing this would not only reduce compliance burdens but would also give the U.S. a competitive edge in digital payments.

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3️⃣ Sen Warren is Wrong: Staking and Mining is Not a “Tax Break”

Senator Warren raised concerns that deferring taxation on staking and mining until sale would create a “tax break” that widens the tax gap. This framing misunderstands both the technology and the economics.

Crypto builders are not asking to avoid taxes. They are asking for rules that make sense. Taxing unrealized staking rewards forces participants to sell part of their holdings every time they earn new tokens, just to cover the tax. That undermines network participation, decentralization, and long-term U.S. competitiveness.

Deferral until sale is not a loophole. In an appreciating market, it actually increases government revenue.

Example:

A miner earns 1 BTC when it’s worth $100,000, and later sells it when it’s worth $200,000.

• If taxed immediately:
  They owe ordinary income tax of 30% on $100,000 = $30,000 now.
  Later, when they sell for $200,000, they owe long-term capital gains tax of 15% on the $100,000 gain = $15,000.
  Total tax: $45,000

• If taxed only when sold:
  They owe ordinary income tax of 30% on the full $200,000 = $60,000.

In this example, deferring tax until the sale raises $15,000 more for the federal government. The difference comes from applying the higher ordinary tax rate to the full value at sale, instead of splitting it between ordinary and lower long-term rates.

The key point: Deferral doesn’t avoid tax, it delays it until value is actually realized, and in many cases, it increases what’s ultimately collected.

4️⃣ Qualified Appraisals: The Easiest Fix on the Table

The qualified appraisal requirement for donated crypto assets might be one of the most outdated rules in the code. It forces taxpayers to obtain formal appraisals for donations, even though digital asset prices are publicly available on major exchanges.

The fix is simple. Allow taxpayers to rely on fair market value data from established exchanges. That would help charities receive more donations, give taxpayers clearer guidance, and provide the IRS more accurate and consistent data. Everyone wins.

This idea received support from both sides of the aisle. It is a rare area of agreement and should be one of the first changes Congress moves forward.

5️⃣ The Bigger Issue No One Solved: The Crypto Tax Gap

While the hearing focused on specific technical issues, the underlying problem is much larger. The United States has a massive crypto tax gap—the difference between what should be reported and what actually is.

Most people who own or trade crypto are not intentionally evading taxes. They are simply overwhelmed.
Tracking every swap, every transfer between wallets, and every micro-gain is too complex for ordinary taxpayers. Even with software, the data is often incomplete or inconsistent.

The result is a compliance system that punishes honest taxpayers who try to do the right thing and rewards those who simply give up.

To close the crypto tax gap, the solution is not more enforcement or more reporting. It is simpler rules and a path for taxpayers to come back into compliance without fear of penalties.

Congress and Treasury should consider creating a voluntary disclosure program specifically for digital assets. Similar to the offshore disclosure programs used for foreign accounts, this would allow taxpayers to correct past reporting issues while avoiding severe penalties.

This would increase compliance, reduce audit backlogs, and generate significant tax revenue. It would also send a clear message that the government wants cooperation, not confrontation, from the crypto community.

6️⃣ Where We Go From Here

The hearing was a good step forward. It showed bipartisan awareness that crypto taxation is not just a niche issue but a core part of U.S. competitiveness and fairness.

But it also showed how much work remains. Lawmakers are still thinking about crypto in old terms: comparing it to gold, gambling, or accounting services. They are not yet seeing how outdated tax rules are holding back both innovation and compliance.

Our job now is to continue the education process. We need to:

• Explain that stablecoins are the future of digital payments and should not be taxed like property.

• Show that staking deferral increases tax revenue, not reduces it.

• Push for a crypto voluntary disclosure program so honest taxpayers can come forward.

• Support straightforward fixes such as the qualified appraisal update.

• Remind policymakers that crypto taxes affect tens of millions of Americans, not just institutions.

My mission is to bring these real-world insights to Washington. Every client we help, every audit we fight, and every policy conversation we join helps shape a system that works for everyone.

The Senate hearing was a positive moment. But awareness alone is not enough. The next step is action, and that starts with rewriting the rules so that everyday investors, builders, and innovators can comply easily, pay fairly, and help America lead in digital finance.

Subscribe below for clear, practical updates on crypto tax reform, real-world case stories, and our ongoing work to bring Main Street crypto to Washington.

Crypto has scored regulatory wins. The bipartisan passage of the GENIUS Act shows that Washington can come together to move crypto forward. Market structure is beginning to take shape. These are major steps, but they only touch parts of the industry. Taxes are different. They touch everyone - every investor, every business, every startup. That is why crypto taxes are the real fight.

Ask any crypto investor what keeps them up at night. The answer is almost always the same: taxes. The system does not work. It is unlike anything else in the American economy.

Traditional taxes are built on withholding, reporting, and checks between third parties and the IRS. With wages, your employer does the work. With stocks, your brokerage issues 1099s and tracks your basis. The infrastructure supports compliance.

Crypto is the opposite. You are on your own. Every swap, every transfer, every wallet, every chain. You are expected to calculate your gains, losses, and basis across thousands of transactions and then defend them in the event of an audit. The tools available are rudimentary. They mishandle complex trades, miscalculate cost basis, and fail to follow assets across chains. Hiring a CPA can cost thousands, but even then accuracy is not assured.

The IRS has made clear it will enforce aggressively. It has created teams devoted to crypto, launched “Operation Hidden Treasure,” and contracted with blockchain analytics firms to trace wallets. Even if you get it right, you must prove it line by line. The burden of proof is entirely on the taxpayer. If your numbers do not align with IRS data, you are presumed wrong until you prove otherwise.

For many investors, the risk of being audited outweighs the risk of underpaying. Some underreport. Some do not report at all. Fear, not clarity, drives behavior. That is not a foundation for a growing industry.

Consider Opportunity Zones. Created in 2017, the program was designed to channel capital into underserved communities. It is a complex program, and participation has been relatively modest—about twenty-one thousand individual investors and a few thousand corporations—but it shows what is possible when policymakers decide clarity matters. The IRS and Treasury produced thousands of pages of regulations, rulings, and guidance to spell out exactly how the program works. That level of effort gave taxpayers and investors a clear set of rules of the road, even if the details are intricate.

Crypto deserves the same treatment. Participation is not modest, it is massive. Roughly one in five Americans now owns some form of digital asset. Yet instead of detailed guidance, taxpayers have only a handful of notices and FAQs to rely on. Entire categories such as DeFi, staking, NFTs, and yield strategies remain undefined. The IRS has shown with Opportunity Zones that it can mobilize quickly when it chooses to. What crypto needs is not thousands of pages of new law, but the same thing investors in Opportunity Zones were given: rules of the road. The difference is priority. Clarity can and should be created for an industry already used by millions of Americans.

Congress has begun to recognize the problem. In meetings I’ve had with both parties, in both the House and the Senate, lawmakers acknowledge that crypto taxes need work. The question is no longer whether crypto should be taxed, but how and when. That is progress. But it is not enough. The fight cannot be left to large industry players and lobbyists alone. Washington responds when Main Street speaks. When lawmakers hear the voices of ordinary investors and small businesses, they listen.

The unfairness in the current system is obvious. Every crypto-to-crypto trade is taxed as if it were a sale, forcing meticulous record-keeping that no stock or bond investor would ever face. Staking rewards and airdrops are taxed the moment they are received, even if the assets are locked or illiquid. Small businesses that accept crypto payments face compliance burdens that are all but impossible to manage. And at every step, the taxpayer must prove their records against an IRS that is arming itself with new reporting rules and powerful analytics.

These are problems I see working with crypto clients everyday. One of my clients was audited over nothing more than stablecoin transactions. The IRS claimed he had more than $100,000 in taxable gains, even though the tokens were designed to stay at a dollar and never moved in value. Each exchange was treated as a sale. The IRS burned resources chasing phantom gains while my client faced crushing stress and the risk of financial ruin for transactions that generated no income at all. That case is still in Tax Court, but it shows exactly how the system fails: outdated rules that turn compliance into punishment.

To move from enforcement by fear to compliance through clarity, we need action at both the IRS and legislative levels. The fixes are not complicated, and most could be implemented today:

• Stablecoins: Treat payment stablecoins as money, not property, so that everyday use does not create phantom gains and endless 8949 filings.

• Staking and Mining: Defer taxation until sale, recognizing rewards as “newly created property.” This aligns tax with economic reality and even increases federal revenue in appreciating markets.

• Cost Basis Accounting: Authorize specific identification with safe harbors at the wallet or exchange level, and permit flexible methods such as HIFO, so taxpayers are not guessing in the dark.

• Charitable Giving: Remove the costly “qualified appraisal” requirement for donating widely traded crypto, allowing reliance on transparent exchange pricing.

• Scam and Theft Losses: Create a safe harbor, modeled on Rev. Proc. 2009-20, that lets victims of fraud deduct their losses under §165(c).

• Voluntary Disclosure: Establish a streamlined program so taxpayers can reconcile past years, certify non-willfulness, and come into compliance without fear of crippling penalties.

Taxes must be fair, clear, and workable. Today, crypto taxes are none of those things. If death and taxes are certain, then crypto’s future depends on building rules that make compliance possible rather than impossible.

The future of crypto prosperity in the United States depends on this fight. Stablecoins and market structure matter, but it is taxes that will determine whether builders stay here, whether businesses thrive here, and whether ordinary Americans feel safe to participate. If we want the U.S. to lead, we need a tax system that is fair, transparent, and clear. That is the foundation of long-term dominance.

This is the fight that matters most, and I am committing myself to it. Winning here means unlocking growth, innovation, and opportunity for every person and every business that believes in the future of American technology.

That is the same opportunity crypto founders deserve today. You should be able to start in a basement or a garage with little more than a laptop and a dream, and still have a fair shot at building something life changing. Right now too many projects face a choice no startup should ever face: hire an engineer or hire a lawyer.

What We Talked About with the SEC

This week we had two rare opportunities to sit down with SEC Commissioner Hester Peirce. First, a large fireside chat with nearly 100 attendees. The next day, a small lunch with just two crypto builders, our client David Fields from ReadyAI, and Commissioner Peirce.

The conversations covered real issues that matter for builders trying to get started in the United States:

• Starting Early- Peirce urged startups to begin conversations with the SEC early, before major fundraising or token launches. She stressed that projects need to be ready to explain themselves clearly, with an elevator pitch simple enough for someone outside the space to understand.

• De Minimis Custody- One of the biggest open questions is whether custody of even small amounts of assets can trigger full custodial regulations. This kind of uncertainty can crush young projects before they start.

• Global Competition- We discussed how the SEC interacts with regulators in other countries. These bilateral conversations can either help or hurt U.S. competitiveness. If rules are too complex here, founders will simply go elsewhere.

• AI-Crypto Overlap- Peirce acknowledged that regulators cannot repeat the mistakes of crypto with AI by shutting the door before innovation even begins.

Learn and stay updated on how policy conversations are shaping the future of crypto in the U.S

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Builders’ Concerns in Focus

What stood out most to me was how seriously Commissioner Peirce took the concerns of small, early stage builders. She wanted to hear not only about high level policy, but also about the day to day realities of trying to launch a crypto project in the United States.

She asked questions like: What is the SEC missing? What obstacles are we not seeing? If you were in charge, what would you do differently?

That level of dialogue is rare. Too often regulators only hear from the largest companies with the deepest pockets. Here, the voices of new projects were elevated.

Our client David Fields had the opportunity to share how ReadyAI is building a decentralized network of AI models on Bittensor, and he raised the issue of token buybacks. Overseas, projects have flexibility to use buybacks to stabilize their networks. In the U.S., the rules are far less clear. Commissioner Peirce listened carefully, asked thoughtful questions, and wanted to understand the nuances. That kind of engagement shows the importance of having builders in the room.

This is exactly the kind of access that can change the future of crypto policy. When the regulator understands that real people are forced to choose between hiring a developer or hiring a lawyer, it reframes the urgency of reform.

Why This Access Matters

For years, crypto’s relationship with Washington felt like shouting into a void. This week showed how much has changed. We now have unprecedented access to policymakers. Not just billion dollar firms, but small builders, early projects, and everyday founders are being invited into the room.

That matters because the people in the room shape the future. When a founder like David Fields can explain his project directly to the SEC, that perspective is carried forward. When builders talk about what it means to choose between an engineer and a lawyer, that story sticks.

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Fighting for U.S. Competitiveness

Here is the bottom line:

• If compliance stays this complex, startups will move overseas.

• If regulation punishes innovation, the next breakthrough will not be born here.

• If builders cannot start from a basement or garage and scale to something transformative, America loses its edge.

Our fight is to make sure that does not happen. To keep the United States competitive in crypto. To give innovators the same opportunity I had when I started my law firm in a basement - to build, to grow, and to change their lives.

The SEC is listening. Policymakers are opening the door. It is on us to keep showing up, telling our stories, and making sure Main Street Crypto has a seat at the table.

Join the conversation—your voice matters in shaping crypto policy

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Last week, I was in Washington, D.C. for a series of meetings on Capitol Hill. I sat down with staffers from both sides of the Senate Finance Committee and with the House Ways and Means Committee majority. The message from all three was clear: crypto taxes are on their radar and the details are being debated.

A few years ago, Senator Ted Cruz joked that not more than five senators could even explain what cryptocurrency was. Fast forward to today, and congressional staff are drilling into nuanced questions about staking income, stablecoin audits, de minimis exceptions, and qualified appraisals. That shift alone should give every crypto investor and builder pause. It shows real progress, but also how much is at stake in shaping the rules of the game.

Senate Finance (Minority Staff)

The first meeting was with staffers from the Senate Finance Committee minority. They came prepared, deeply familiar with the provisions of the Lummis digital asset bill:

• No tax on staking/mining until sold

• De minimis exemption for small transactions

• Qualified appraisal reform

They asked what issues weren’t already in the bill. They pushed hard on the staking issue: if stakers are performing a service and getting rewarded, why shouldn’t that be treated as taxable income immediately? Is it really “self-created property,” or is it closer to being paid for work performed?

These are fair, difficult questions. And the fact they’re being asked shows genuine engagement, not dismissiveness, but an effort to work through problems constructively. We also discussed the unfairness of requiring qualified appraisals in IRS audits, where taxpayers face costs and burdens that make little sense.

The takeaway: minority staff see crypto as an area that needs bipartisan solutions, and I am optimistic about Democrats getting involved to make that possible. From the level of preparedness they showed, it seem crypto tax reform is likely to be on the docket by year’s end.

Senate Finance (Majority Staff)

The next conversation was with Senate Finance majority staff. Again, they knew the issues. The first focus here was on the de minimis exclusion, the idea that small crypto transactions shouldn’t trigger a tax event.

Their concern: abuse. If we only allow a per-transaction limit, could people game the system? Would an aggregate cap work better? But then again, if taxpayers have to track an annual cap, does that really solve the record-keeping nightmare?

This is the kind of nuanced thinking we need in D.C. The goal is to cut down on absurd reporting requirements, not just create a new layer of complexity. We discussed different approaches: per-transaction limits, aggregate caps, or a hybrid of both.

Another major point: while many fixes could theoretically be handled by the IRS through administrative guidance (such as staking, mining, and qualified appraisal reform), staff emphasized the importance of durability. Rules issued by the IRS today could be undone by the next administration. Laws, once passed, last longer. That’s why legislation is the preferred path.

House Ways and Means

The final stop was with the House Ways and Means majority staff. Their opening line was striking: “As a preface, we’ve been thinking a lot about crypto tax issues.”

That set the tone for a high-level, detailed discussion:

• Stablecoins: Staffers recognized that after the GENIUS Act, stablecoins are in the spotlight. But they also understood that taxing every stablecoin transaction is absurd. I shared client stories of audits focused solely on stablecoins, where the purpose of the asset is commerce, not speculation.

• De minimis: We again dug into aggregate limits and how to design them fairly.

• Qualified appraisals: They wanted to know how to prevent abuse, such as pumping the value of illiquid tokens before donating them. We discussed solutions like limiting donations to tokens listed on U.S.-regulated exchanges.

• Foreign persons & sourcing: Staff asked detailed questions about non-U.S. persons using U.S. exchanges for staking or starting mining businesses here. How do we ensure fairness while keeping the U.S. competitive?

• Staking and mining as a business: This issue isn’t even in the Lummis bill but came up in our meeting. When does staking or mining rise to the level of a business eligible for deductions? This matters as staking becomes more common, and right now, taxpayers are left guessing.

Personal Reflection

What struck me most about this trip was the tone. Even a year ago, I was walking senators through the basics and explaining why crypto mattered for our future. Back then it felt like giving a crash course. This time it was different. The staff already knew the issues. They weren’t asking “what is crypto” but instead debating how to design exemptions, prevent abuse, and write rules that will last.

That shift shows that crypto has moved firmly into the mainstream of policy. It also tells me that the window for meaningful reform is open right now. We cannot waste it.

The Big Picture

Taxes touch everyone. Individuals, families, small businesses, large companies. No one escapes them. Right now for crypto, taxes are broken. The rules are confusing, burdensome, and unfair. But they are not set in stone. They can be fixed.

That is why this moment matters. Washington is paying attention. Lawmakers are asking the right questions and they want to get this right. But they need to hear from us. They need to hear the real stories of how crypto taxes are hurting innovation, slowing adoption, and making life harder for ordinary people who are simply trying to participate in this new economy.

This is our shot. If we bring our voices together, we can make sure the solutions that come out of Washington reflect the needs of both individuals and businesses, large and small. The window for reform is open right now. Let’s make sure we use it.

Stay tuned for updates, and if you have a story of how crypto taxes have impacted you, I want to hear it. Stories matter in D.C., and together, they can shape the fight.

Message me and tell me how crypto taxes or regulations have impacted you.

Don Jr has long been an advocate for technology, business, and market freedom. What makes him important for crypto is not only his proximity to power but his personal story. The Trumps were effectively forced out of banking for political reasons. Major financial institutions blacklisted them, shutting down accounts and denying access. For most families, that would be the end of the road. For Don Jr, it was a reason to explore alternatives, and that journey led him into crypto. He has become a behind-the-scenes voice encouraging his father to take crypto seriously.

Fast forward to today, and the Trump orbit is not “interested” in crypto, they are deeply embedded. Just this week, the launch of World Liberty Financial’s stablecoin marked another step forward, signaling that the movement is not just about speculation. It is about creating a parallel financial system that can withstand political weaponization. President Trump himself has gone further than any U.S. president in embracing crypto, showing not only that it has a place in our economy but that it is central to future American innovation.

Against that backdrop, I had the opportunity to join Don Jr in Chicago on August 29th for a small lunch with about ten attendees — business leaders, political leaders, and advocates from across Illinois.

Crime, Cannabis, and the Banking Problem

The conversation was wide-ranging. Crime in Chicago was front and center, with discussion about whether the National Guard should be deployed to restore order. Local representatives expressed strong support for measures that could finally make the city livable again.

We also spent time on cannabis. Federal and state laws are hopelessly out of sync, and as a result, legal businesses and their workers face immense challenges. From renting apartments to getting mortgages, even to holding a simple bank account, everything is harder. It was in that moment Don Jr pointed out that he had lived through a similar experience. His family had been pushed out of banking because of politics. Crypto became not just a tool but a lifeline.

The parallel was striking. When the traditional financial system becomes politicized, the only answer is building a system that cannot be shut down. That is exactly what crypto promises.

Stablecoins and the IRS Problem

I raised one of the most frustrating issues I deal with as an attorney. Just last week, I worked with a client who was audited for stablecoin reporting. Stablecoins are designed to be one-to-one with the dollar. They are not “investments” in the traditional sense. Yet, under current IRS rules, every transfer, every movement is technically taxable. This creates absurd compliance burdens. It is the kind of issue that discourages innovation and hurts ordinary people.

Stablecoins should be the simplest bridge between crypto and the dollar, yet right now they are treated with suspicion. Don Jr was engaged on this point, and other attendees echoed how the rules are stifling business creation.

I’d love to hear how crypto has impacted your life—message me here with your story. These voices matter.

The Future: Beyond the Biden Years

There was broad agreement in the room: the Biden administration has been catastrophic for crypto. From weaponized regulators to hostile policies, the goal has been clear — to choke crypto out of existence. But the future does not have to look like that.

What we discussed was how to ensure that pro-crypto policy extends beyond one administration. That this is not just a four-year experiment, but a generational shift. History will look back on these years as the early days, much like the internet in the 1990s. Those who built then laid the foundation for trillions in value creation. Crypto is no different. This is the opportunity for Main Street Americans to build wealth, and it is an opportunity that requires political leadership to protect.

Building Momentum in Illinois

Beyond the formal discussion, the day gave me the chance to connect with Illinois leaders. One former gubernatorial candidate was particularly interested in how crypto could improve state government operations. Others were eager to understand how policy could create jobs and keep innovation here rather than push it overseas.

Later, I joined the motorcade to a fundraising event in the suburbs. That ride alone was valuable — it allowed me to speak with more Illinois politicians and advocates about what we are fighting for. These conversations reinforced something I’ve seen again and again: most politicians are still at the early stages of understanding crypto. But the fear is gone. Elizabeth Warren’s scare tactics no longer hold the same weight. Everyone now knows someone who got rich off crypto, or someone who lost access to billions. The stories are real, and they create curiosity.

The question I kept hearing was the same: is it too late? And my answer was clear. No. Buying Bitcoin today is not too late. Building a crypto business today is not too late. Supporting pro-crypto policy today is not too late. We are still early.

Why It Matters

What struck me most about spending the day with Don Jr was how personal this issue is to him. This is not a scripted talking point. It comes from lived experience. And that makes all the difference.

Crypto is not just about charts and speculation. It is about freedom, access, and resilience in the face of a financial system that has been weaponized. The Trumps understand that better than most. And as new projects like World Liberty stablecoin launch, it is clear that the future of crypto is not just theory. It is happening right now.

The real question is whether America will lead or fall behind. That depends on the choices we make today.

That’s why I’m excited to share an important opportunity happening here in Chicago on September 15th: SEC Commissioner Hester Peirce, one of the few regulators in Washington consistently fighting for crypto innovation, will be visiting to meet directly with builders and investors.

Why Hester Matters

Commissioner Peirce has been a leading voice for fairness and clarity in crypto regulation. Appointed to the SEC in 2018, she has earned the nickname “Crypto Mom” for her willingness to challenge the agency’s heavy-handed enforcement approach and push for clear rules that give entrepreneurs room to innovate. She has advocated for safe harbors for token projects, protections for small builders, and a regulatory environment that encourages—not stifles—new ideas.

Simply put, Hester Peirce has been one of the strongest allies our community has in Washington.

Her proposals for a safe harbor framework for token projects demonstrate her commitment to giving builders the breathing room they need to innovate without fear of arbitrary action. Equally important, she has long questioned the accredited investor definition, a rule that effectively tells Americans what they can and cannot invest in, based not on knowledge or risk tolerance but on income and wealth.

I’ve spoken with Commissioner Peirce about this issue directly, and she has been clear: it is unfair to lock everyday people out of opportunities simply because of their financial status. Crypto should be open to everyone, not just the wealthy or well-connected.

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A First-of-Its-Kind Builder Roundtable

Together with the Crypto Task Force, Commissioner Peirce is hosting a private roundtable in Chicago on September 15th with a small group of early-stage builders. This is an opportunity for our supporters to directly share their stories and perspectives with the SEC.

If you are a builder and want to be considered for participation, please reach out to me directly. This is our chance to make sure the voices of innovators are heard where it matters most.

Fireside Chat – September 15th at 5:00 PM

We are also proud to sponsor a fireside chat with Commissioner Hester Peirce, hosted by the Illinois Blockchain Association.

📍 CoinFlip, 433 W. Van Buren St, Chicago, IL 60607
📅 Monday, September 15th
🕔 5:00 PM – 8:00 PM

Space is limited and registration is subject to approval. Please register here: Request to Join

This event will feature a social gathering followed by a conversation moderated by Will Lawson, a Chicago-based founder and IBA board member. It’s a chance to hear directly from Commissioner Peirce and connect with other leaders building the digital future.

Standing Up for Fair Markets

Commissioner Hester Peirce has consistently reminded Washington that the SEC’s job is to protect investors and ensure fair markets, not to dictate which technologies survive or who gets access to opportunities. Her visit to Chicago is a chance for our community to directly shape the conversation about the future of crypto.

If you are a builder, this is your opportunity to make your voice heard at the roundtable. If you are an investor or supporter, join us at the fireside chat to show that the demand for freedom, fairness, and innovation in crypto is strong here in the Midwest.

Meeting with Andrew Rittenhouse

Andrew Rittenhouse, one of the key contributors to the White House Report, emphasized the importance of feedback from practitioners like myself. He encouraged me to share critiques - what the report covered well, what it overlooked, and where more focus is needed.

We talked broadly about areas where administrative action could move the needle, such as the IRS’s FAQs on digital assets and how Treasury’s Office of Tax Policy sets the direction for much of this work. He also highlighted that certain senators, including Senator Lummis, Senator Scott, and Senator Moreno, are expected to play important roles on crypto-related legislation.

In a symbolic gesture, he handed me a copy of the White House Report -personally signed - which I’ll keep as a reminder of this pivotal moment in digital asset policy.

Meeting with Tyler Williams

Tyler Williams, also a co-author, works at the Treasury’s Office of Tax Policy. He explained that the report is only a starting point, and feedback from attorneys and tax professionals is essential to refining future guidance.

One area we touched on was cost basis allocation, a major issue for nearly every crypto investor but notably absent from the report. Tyler encouraged me to send him additional information on this topic, as it’s something directly affecting my clients.

He also outlined Treasury’s priorities going forward: immediate focus on guidance related to the recently passed GENIUS Act, followed by market structure, and then implementation of the broader White House plan.

Like Andrew, Tyler also signed my copy of the report, which now carries not just ink but the weight of responsibility to keep pressing these issues forward.

Why This Matters

These meetings confirmed what I’ve long believed: the future of crypto taxation and regulation will be shaped not just by Congress, but by administrative guidance from the IRS and Treasury. Practitioners, business owners, and everyday investors all have a stake in ensuring that policies reflect the realities of this industry—not just abstract theories.

My role, and the role of many in the crypto community, is to make sure policymakers hear the real stories: how current rules affect taxpayers, what’s working, and where the gaps remain. The White House Report is an important milestone, but it’s only the beginning.

Your Voice Matters

As I continue these conversations in Washington, I want to bring your stories with me. If you’ve faced unfair tax treatment, confusing rules, or unnecessary burdens because of crypto regulations, share them with me. These firsthand accounts help demonstrate to policymakers why reform is so urgently needed.

By subscribing here, you’re not just keeping up with policy updates—you’re joining a movement to make sure everyday investors and builders are heard in DC. Together, we can ensure that the next chapter of digital asset regulation is written with all of us in mind.

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We cover the new standalone crypto tax bill in Congress, IRS-level changes we’re recommending, and why your stories matter more than ever in shaping policy. This is not just about Wall Street or institutions, the people in DC want to hear from us.

Watch the full briefing to understand where things stand, what’s ahead, and how you can be part of making crypto tax rules fair and workable for everyone.

Meeting with Senator Cynthia Lummis (July 29, 2025)

I met with Senator Lummis along with Chris Land and Conner Brown, two of her senior staff. The main topic was the crypto tax policy, including the crypto tax amendment originally introduced during the OBBB process. Senator Lummis explained that while the amendment initially gained support, it lost momentum as scoring for tax revenue became a sticking point.

The proposal combined two key pieces:

• Wash sale rules applied to crypto (which increases tax revenue scoring)

• A de minimis exemption (which reduces revenue scoring).

Originally, the exemption was set at $600, but in negotiations it dropped to $300 to try to improve the score. Senator Lummis expressed her view that a more effective and manageable approach would be to exempt a flat amount of gains (ie. up to $5,000 annually) regardless of transaction count.

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She noted that a standalone bill now exists with the same provisions as the OBBB amendment, but it will require the support of Senator Crapo and the Senate Finance Committee to advance. Another potential vehicle could be the second reconciliation process later this year.

We discussed how these issues are not abstract - they affect my clients directly. I shared a story of a client who donated $500,000 in bitcoin to charity. The IRS not only disallowed the deduction, but also imposed an accuracy penalty, citing the “qualified appraisal” rule. Only after threatening Tax Court did the IRS back down. Senator Lummis and her team were very interested in this example, since her bill directly addresses this rule. Her team asked that we share more examples with them.

Senator Lummis and her staff agreed that many of the legislative fixes in her bill are necessary precisely because of administrative overreach by the IRS, from revenue rulings to informal memos that unfairly shaped policy.

Her team also asked that we prepare a document outlining the top crypto tax issues that can be solved administratively, including real client stories. We are working on this presently.

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Meeting with Senator Marsha Blackburn (July 30, 2025)

The following day, I met with Senator Blackburn and her legislative aide, Andrew Guffee. Senator Blackburn was direct in her assessment: the crypto tax amendment did not gather much support during the OBBB process. But she made clear her plan is for crypto tax legislation to advance before the end of the year.

She noted that the House is already working on a draft bill. However, other priorities may move ahead first. The GENIUS Act faced intense pushback, and while CLARITY remains a major focus, she suggested that a Bitcoin Reserve bill may arrive sooner, given its standing as an administrative priority.

When it comes to the IRS, Senator Blackburn emphasized that the agency ultimately takes its direction from Congress on crypto taxation. This underscores the importance of getting clear, workable legislation passed.

After our meeting, I spoke further with Andrew Guffee, who serves as her advisor on crypto policy. He mentioned that the Senate Banking Committee may be holding hearings on crypto taxes later this year which could provide an opportunity for us to be heard.

Why These Conversations Matter

Both meetings reinforced why our advocacy is essential. Senators Lummis and Blackburn understand that crypto tax policy is not just about abstract rules, it’s about real people, real businesses, and real innovation being stifled by outdated or misapplied laws.

From pushing for de minimis exemptions that make everyday transactions workable, to fighting back against IRS overreach on charitable donations, these senators are helping move the conversation forward. But they are also clear-eyed: passing reform will take bipartisan cooperation, pressure from constituents, and persistent engagement from those of us in the trenches.

That’s why we’ll continue to show up in Washington, share the stories of everyday crypto investors and builders, and make sure that the voices shaping policy aren’t just the loudest lobbyists, but the people building and using this technology every day.

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