Crypto Tax, International Structures & Stablecoin Payments in 2026: Key Insights from The On Chain Podcast Ep. 3

In Episode 3 of The On Chain Podcast, Tax On Chain co-founders Rafael Franco and Oliver Woodbridge sit down with Harrison Dell, one of Australia’s leading crypto tax lawyers, founder of Cadena Legal, founder of Blacksheep (a stablecoin payments business), and part-time internet celebrity with a following built on TikTok.

Harrison has spent the last four years building Cadena Legal into one of the few law firms in Australia genuinely specialised in crypto and international tax. Along the way he has built a strong reputation as a clear, direct voice on Australian tax policy, and quietly built a fintech business solving real cross-border payment problems for businesses.

From crypto tax and international relocation planning, to stablecoin infrastructure and the future of AI-driven professional services, this episode explores the trends reshaping how globally mobile investors and businesses operate in a digital world. 

🎙️ Listen to the Full Episode Here:

Going From Tax Office Auditor to Niche Crypto Lawyer

Rafael opened by taking Harrison back to how he actually ended up in crypto tax law. Like a lot of niche careers, it happened by accident.

Harrison started Cadena Legal in 2022 after beginning his career at the Australian Tax Office (ATO) before spending several years in traditional tax advisory roles at other firms. The crypto specialisation built itself, largely because people kept asking him about it. He had done some crypto work years earlier at the ATO, but it was social media (specifically TikTok) that really accelerated his client base.

“I remember he said to me, oh, it’ll take a good sort of six months before you see a lead come through. It took a week.” ⏱ 5:09 – Harrison Dell, Cadena Legal

What followed was a streak of high-value clients, most of them found Harrison through Tik Tok, recognised his face from short-form content, and converted at a rate most law firms would envy. His niche focus and a willingness to actually use the products he was advising on (DeFi, smart contracts, wallets, even taking losses to understand how scams work) gave him a credibility most generalist tax lawyers cannot replicate.

“You’re not going to understand what the product is, the token or whatever, unless you try and use it. Unless you at least have that. How does a wallet work? How do I use a smart contract? How am I going to stuff it up? What does a scam look like?” ⏱ 12:42 – Harrison Dell, Cadena Legal

Both Harrison and the Tax On Chain team agreed: clients can tell when a professional lacks genuine expertise, especially crypto clients. Niching down is what makes the difference.

How the Crypto Client Base Has Evolved Since 2021

Four years ago, Cadena Legal’s book was 80 to 90 percent crypto and crypto-adjacent. It was peak NFT and Defi season: 19-year-olds with multi-million-dollar JPEG portfolios, DeFi farmers, Strong Node holders, and anyone who could spell “yield farming”. Some managed to cash out before the market turned, but many didn’t and round tripped their “paper” gains.

Today the split looks very different: roughly 50 percent crypto or crypto-adjacent, 30 to 40 percent international tax, and the remaining 10 percent everything else. The crypto clients themselves have also matured.

“It’s a lot more sophisticated now. You’ve got DeFi products, stablecoins, and they’re not completely full of [it] because most of those projects are dead. The ones still going have generally pivoted to all sorts of things.” ⏱ 23:49 – Harrison Dell, Cadena Legal

Rafael and Oliver noted the same pattern at Tax On Chain. Fewer crypto clients per dollar of revenue, but significantly larger engagements. The retail NFT speculator has been replaced by sophisticated traders running prop strategies, bot sniping and long-term holders wanting tax and structuring advice.

Harrison’s take on it: the space is genuinely maturing. It is no longer about memecoins and PFP projects. It is about people building real financial products and using the infrastructure to capture value.

International Tax Structures: What Actually Works (and What Doesn’t)

The fastest growing part of Cadena Legal’s book is international tax. A lot of that demand is being driven by Australians who want to leave, or at least restructure offshore. Harrison was direct about why.

“We charge a lot of tax. It’s just not feasible.”.” ⏱ 9:50 – Harrison Dell, Cadena Legal

The biggest misconception Harrison hears? That you can simply move overseas, sell your Bitcoin or XRP, and walk away tax-free. Australia has rules against exactly that. You either pay tax on your assets at exit, or you pay tax in Australia once you eventually sell when you are overseas. Getting on a plane to Dubai does not solve the problem.

A few other patterns Harrison flagged:

• Dubai used to be the default. Prior to the Iran conflict, a lot of clients said “I want to move to Dubai” without ever having visited. Harrison’s standard question was “have you been there?” The honest answer was usually no. Lifestyle is a consideration often overlooked.
• You have to genuinely commit. Two or three years minimum, with real local connections. If your family stays in Australia and you are casually overseas, the planning collapses.
• New Zealand’s transitional tax resident regime is a great option for the right person, and substantially easier to access than Dubai.
• Indonesia and Thailand are increasingly common, though Thailand is tightening.
• Cayman, BVI and Panama serve different purposes. Cayman is built for funds and head company operations. BVI is similar but lighter on compliance. Panama is “coming up in the world”, in Harrison’s words.

The technical point Harrison made that most people miss: jurisdictions like Cayman are not “dodgy” just because they are tax havens. They are highly regulated, transparent, and built for a structural purpose, which is allowing investment funds to operate legitimately. Australia’s tax system and regulatory environment is not built for that role, which is part of why so much global capital is structured around it rather than through it.

“If you don’t have those local connections, you’ve got to build them. I’ve had a lot of people go and then they build them there. That’s fine. But you really got to commit.” ⏱ 28:51 – Harrison Dell, Cadena Legal

The Crypto Asset Reporting Framework (CARF)

The Crypto Asset Reporting Framework (CARF) is coming. Australia has not yet legislated it, but exchanges are already planning so they can comply with the reporting requirements. Harrison flagged a few real problems with how this is being implemented.

On having to collect TFNs from customers: “There is no penalty for not providing it. There is no withholding tax. They [the exchanges] just go, well, we can’t service you. It also creates a big honeypot.” ⏱ 1:04:25 – Harrison Dell, Cadena Legal

CARF is not unique to Australia – it is a global tax reporting framework developed by the OECD. The framework is primarily aimed at cross-border tax information sharing between participating jurisdictions. Once implemented, crypto-asset service providers (e.g. exchanges) in participating jurisdictions will report information relating to Australian tax residents, which will then be shared with the ATO through international exchange agreements. Australia’s proposed implementation appears broader, extending reporting obligations to domestic Australian customer activity as well. 

For the Bitcoiners and sovereign-leaning crypto OGs, and anyone already frustrated by digital ID requirements, this is likely to be the final straw. Harrison expects a meaningful shift toward self-custody and away from centralised exchanges, particularly among long-term holders who simply do not want to hand over a TFN and to a fintech or are opposed to the government having oversight of their transactional data.

The catch: if they do eventually sell, they will still have to come back through the regulated system.

The ATO, Crypto Enforcement, and What Is Actually Being Audited

Harrison has had one full crypto ATO audit. Tax On Chain has had several ATO reviews, each of which were dismissed after the ATO was satisfied with the reporting. The picture is consistent: the ATO is currently only meaningfully looking at centralised exchange data. The trigger is almost always large AUD off-ramps.

“It’s all still there [public blockchain data]. So when the day comes that they do look at it, they’ll see all the dirty laundry.” ⏱ 59:16 – Harrison Dell, Cadena Legal

The ATO has flagged that their crypto team is expanding next year, with a substantially bigger budget. But the capability gap on onchain data remains. Regardless, the blockchain itself is a permanent record, which is why simply not declaring onchain activity is a strategy with a very long tail of risk as the ATO’s capabilities will eventually catch up.

The “Ten Men at the Pub” and Australia’s Tax Reform Problem

One of the highlights of the episode was Harrison’s retelling of the classic ten-men-at-the-pub tax anecdote, used to illustrate how tax reform actually plays out in Australia. Ten men buy beers. The wealthiest pays the lion’s share. When prices drop, the wealthy man saves the most in absolute terms, which sparks outrage from everyone else. Eventually, the wealthy man stops coming – leaving everyone else to cover a larger share of the bill.

“And that’s kind of the cycle that we go through. We put a lot of tax on stuff and then the people with movable assets will just go. Even if they pay an exit tax, they will just go. The only ones we keep is mining, oil, gas, and houses.” ⏱ 1:09:21 – Harrison Dell, Cadena Legal

Harrison’s broader point: Australia has not had genuine tax reform since the GST in the late 1990s. Everything since has been tweaking the edges. The result is a system where the easiest taxable base (high-income PAYG earners, particularly doctors and professionals) carries an outsized load, while genuine wealth, which is harder to tax, sits in structures that the system was never coherently designed for.

The 50% CGT Discount and What the Budget Might Bring

This conversation was recorded pre-budget, and at the time there was active speculation that Treasury was considering changes to the 50% CGT discount. Harrison’s view on the speculation cycle was sharp.

“These are intentional leaks because we are the focus group. They look at the public response.” ⏱ 1:17:40 – Harrison Dell, Cadena Legal

Treasury models everything. The Parliamentary Budget Office costs every conceivable scenario. Leaks to outlets like the AFR are a way of testing public reaction before committing. By the time it lands in the budget, the political team has already seen enough sentiment data to make the call.

The Tax On Chain team has fielded plenty of panicked emails from clients asking whether to restructure now. The answer in almost every case: don’t act based on whispers. Decisions on structural changes should be based on actual policy, not speculation.

Black Sheep: Building Stablecoin Payment Infrastructure

Harrison’s second business is Black Sheep, a stablecoin payments platform. Think Airwallex or Wise, but with the ability to send and receive stablecoin payments alongside traditional fiat FX.

The product is not really aimed at retail. It is built for businesses with cross-border payment needs, particularly importers and exporters in Asia-Pacific where suppliers increasingly prefer USDT for fast settlement.

“If my supplier from China or Hong Kong or Singapore says, we need USD in the account before we’ll open the containers for you, and you have to send it by Swift, that’s going to take T plus 2, T plus 3, maybe longer. But if it’s AUD to USDT, we collect the AUD, swap it immediately into USDT, and it’s gone in 30 minutes or less.” ⏱ 1:23:32 – Harrison Dell, Cadena Legal

Harrison was direct about what stablecoins are actually useful for. They are not a holding asset. They are a payment and FX tool. Their value is in moving money across borders quickly, particularly into corridors that traditional banking treats as exotic.

He was equally direct about Australian stablecoins. AUDF, in his view, is the most useful of the new entrants, primarily because it offers genuine one-to-one minting and burning with no fees, and the issuer (Forte) has real FX liquidity behind it. But the use case for AUDF is wholesale and operational, not retail accumulation.

“The best use of an AUD stablecoin is to sell it for a USD stablecoin. Which really says the purpose of these stablecoins is for payments, not trading.” ⏱ 1:28:14 – Harrison Dell, Cadena Legal

The Future of Stablecoins as Invisible Infrastructure

Looking forward, Harrison expects stablecoins to follow the same trajectory as wallets: invisible infrastructure powering things people use every day, without those users ever needing to know they are signing blockchain transactions.

Embedded wallets, social sign-on, pass-key based custody, and account abstraction have already made the seed-phrase-on-a-metal-plate model feel dated. The next layer is institutional adoption of stablecoin rails for cross-border settlement, with banks and incumbent payment networks building on top rather than being displaced by them.

Ripple has pivoted hard into cross-border payments and is, like Black Sheep, network-agnostic on the underlying stablecoin. Circle’s Payment Network is doing similar work. None of them are betting on a single winning stablecoin. They are betting on the infrastructure to move between them.

Africa: The Next Growth Frontier

One of the more interesting tangents was on why Black Sheep is targeting Africa next.

“Africa is sort of like how Latin America was three, four, five years ago when they just had this economic boom and the middle class grew massively.” ⏱ 1:35:30 – Harrison Dell, Cadena Legal

The thesis: African countries do not love their own currencies (hyperinflation, weak central bank credibility, FX restrictions), local engineering talent is being increasingly paid through global remote work, and stablecoins are already the default payment rail for that workforce. A platform that can collect local currencies and pay out in USDT serves a market that is growing faster than most of the rest of the world.

Australian Crypto Tax Q&A: Residency, Moving Overseas & Stablecoins

Tax On Chain is a specialist Australian crypto tax accounting firm. The answers below are general in nature, address Australian tax consequences only, and do not constitute personal financial or tax advice. Foreign tax outcomes will depend on the laws of the country you move to and should be assessed by a qualified adviser in that jurisdiction. Individual circumstances vary. Speak to a qualified crypto tax adviser before making decisions.

Do I still pay Australian tax on crypto if I move overseas?

It depends on whether you have actually ceased Australian tax residency. If you remain an Australian tax resident while living abroad, your worldwide income, including all crypto gains, staking rewards, DeFi yield, and disposals, remains assessable in Australia regardless of where you physically live.

If you have genuinely ceased Australian tax residency, you generally only pay Australian tax on Australian-sourced income going forward. However, the act of ceasing residency itself triggers a deemed disposal of most of your CGT assets (including crypto) at market value on the day you leave, which is a CGT event in Australia. You can elect to disregard this in some cases, but that election has its own consequences when you eventually sell.

Am I still an Australian tax resident if I move overseas for work?

Possibly. Moving overseas for work, even on a multi-year contract, does not automatically end your Australian tax residency. The ATO applies four tests, and you only need to fail one to remain a resident.

The most commonly missed test is the “resides” test, which looks at where you ordinarily live based on the totality of your circumstances. If your family stays in Australia, if you keep a home here, if your social and economic ties remain Australian, and if your absence is treated as temporary, you are likely still a tax resident even if you are physically overseas for years.

The “domicile” test is also significant. Even if you are physically absent for an extended period, you remain an Australian tax resident unless you can demonstrate a permanent place of abode outside Australia.

This is one of the most contested areas of Australian tax law, and getting it wrong is expensive. Tax On Chain works through residency analysis with clients individually before they leave, not after.

How long do I need to live overseas to stop paying tax in Australia?

There is no fixed time period. You do not stop being an Australian tax resident simply because you have been overseas for more than 12 months, two years, or any other arbitrary period.

What matters is whether you have genuinely shifted the centre of your life overseas. The ATO looks at where your permanent home is, where your family lives, where your assets are, where your bank accounts sit, your immigration status in the new country, and the pattern and intention of your absence.

As a practical matter, ceasing Australian tax residency typically requires a multi-year commitment with real local roots in the new country. People who try to “ghost” Australia while keeping a foot in the door (family here, property here, frequent visits back) usually find they have never actually become a non-resident, and can end up with significant assessable income they failed to declare.

Can the ATO tax my crypto if I move to Dubai or another tax haven?

If you remain an Australian tax resident while living in Dubai, then yes. Australian tax residents are assessed on worldwide income, meaning crypto gains, staking rewards, and other income earned while overseas is still assessable in Australia. Simply moving overseas does not automatically cease your Australian tax residency – whether you remain a resident depends on Australia’s residency tests which consider factors such as the permanence of your move, where you ordinarily live, and your ongoing ties to Australia. 

If you have genuinely ceased Australian tax residency and are living in Dubai, then your post-departure crypto activity will generally fall outside the Australian CGT net. However, when you cease Australian tax residency, a deemed disposal event can apply to your crypto holdings at their market value on that date, effectively bringing any unrealised gains into the Australian tax system at that point (unless an election is made to defer the taxing point, which can have consequences later on).

It is a common misconception that you can simply move overseas and sell crypto tax-free. In reality, whether Australia can continue taxing your crypto depends on your tax residency status, and ceasing Australian tax residency is often far more complex than simply relocating overseas.

 

What happens to my Australian crypto holdings when I become a non-resident?

When you cease Australian tax residency, you are generally deemed to have disposed of your CGT assets that are not classified as “taxable Australian property” at their market value on the day of departure. For most Australian crypto investors, this would typically include their entire crypto portfolio.

The deemed disposal triggers a CGT event in Australia, even though no actual sale has occurred and no cash has changed hands. The gain (or loss) is calculated as the difference between the AUD market value of the crypto on the day of departure and your original cost base. If the gain is significant, this can create a substantial tax liability.

You can elect under Section 104-165 of the ITAA 1997 to disregard the deemed disposal for some or all assets. If you make this election, the assets are treated as taxable Australian property, meaning they remain within the Australian CGT net even after you become a non-resident. When you eventually sell, the full gain (calculated from your original cost base) becomes assessable in Australia, regardless of where you are living.

This election is irreversible and the trade-offs are highly individual. Tax On Chain works through this analysis with clients before departure, modelling the tax outcome under both options against the actual structure and timing of any planned disposals.

What does the implementation of CARF mean for crypto investors?
CARF represents a major shift in how crypto activity will be monitored and reported globally. Under the framework, participating exchanges and digital asset service providers will be required to report customer information and transaction data to tax authorities, with that information then shared internationally between participating jurisdictions, including the ATO.

In practical terms, this means the ATO will likely have significantly greater visibility over crypto activity than ever before – including activity that historically may have sat outside traditional financial reporting systems. While on-chain activity itself is not being directly reported under CARF, the increasing linkage between wallets, exchanges, KYC data and blockchain analytics means it will become substantially more difficult for investors to remain outside the tax system altogether. As a result, maintaining accurate records and ensuring crypto tax affairs are up to date will become increasingly important.

 

What records do I need to keep for crypto if CARF reporting starts?

Under CARF, the reporting obligations generally only apply to digital asset service providers such as exchanges and trading platforms – not individual investors directly. Broadly, participating exchanges will be required to collect and report information such as your identity, wallet addresses, account balances, and crypto transaction activity to tax authorities, which may then be shared with the ATO.

As an individual investor, you will not need to lodge separate CARF reports yourself. However, you will still need to maintain accurate records of your crypto activity to ensure your tax returns can be properly prepared and reconciled against the information being reported to the ATO by exchanges and other providers.

 

When is the best time to restructure a crypto portfolio?
One of the best times to restructure is often when your portfolio is sitting on unrealised capital losses or is trading close to its overall cost base. This is because transferring crypto between entities (for example, from your personal name into a trust or company) is generally treated as a disposal for CGT purposes. If significant unrealised gains exist, the restructure itself can trigger a substantial tax liability, which you want to avoid.

In practice, weaker market conditions or periods following major drawdowns can create valuable restructuring opportunities, allowing investors to reposition assets into more appropriate long-term structures before the next major growth cycle. That said, these strategies need to be approached carefully to ensure they do not trigger the ATO’s anti-avoidance provisions, particularly where transactions lack genuine commercial purpose. 

 

How does Tax On Chain help Australian crypto investors?

Tax On Chain is an Australian accounting and advisory firm specialising in cryptocurrency and digital assets. Founded by Rafael Franco and Oliver Woodbridge – who also host The On Chain Podcast – the firm advises high-net-worth individuals, SMSFs, crypto-native businesses, and also provides forensic accounting services in criminal and family law matters.

Tax On Chain is Australia’s leading specialist crypto accounting firm, staffed by a team of Chartered Accountants with deep expertise across the digital asset industry. The firm’s clients span the full spectrum of the crypto economy, from retail investors and SMSF trustees through to some of Australia’s most successful traders managing portfolios exceeding $100M, global institutional staking providers, and founders building digital asset businesses.

Services include tax compliance, structuring and tax planning advice, crypto tax returns, crypto reporting, crypto SMSF establishment and compliance, and accounting support for crypto businesses.

 

Book a consultation: taxonchain.io

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Connect with the experts featured in this episode:

• Tax On Chain – crypto tax accounting for individuals, businesses and SMSFs: taxonchain.io
• Mortgage On Chain – specialist mortgage broking for crypto investors: mortgageonchain.com.au
• Cadena Legal – Australian crypto and international tax law: cadenalegal.com.au
• Black Sheep – stablecoin payments for Australian businesses

The content in this podcast is for informational purposes only and does not constitute financial, tax, or legal advice. Please consult a qualified professional before making investment decisions.