Important: this episode is not legal, tax or financial advice. Tony shares his experience and views. We checked the legal figures below against the official texts as of 18 October 2026, but your position depends on your residence, structure and type of income. Make decisions with a specialist.
Tony Maysky calls himself “a startup lawyer by nature”. He worked at Sumsub, one of the world’s largest KYC providers: the head office is in London, but according to Tony the decision-makers sat in Cyprus. Now he and his colleagues have founded Point Legal, a law firm for small companies “that will later become big ones”, and he is also building a Legal AI product.
The conversation with Katerina covers three topics: why lawyers become a bottomless cost in a growing company, where AI helps lawyers and where it makes things up, and why Cyprus suits founders. The most practical part is about capital gains: below we compare what Tony says with what the law says.
Contracts: from one lawyer to twenty
At the company where Tony worked, contracts were first handled by one person, then ten, then twenty, and twenty still weren’t enough. Tony calls it “an insane cost center”. Every new client means reviewing the contract, new drafts, the client’s requested changes, explaining why a clause can’t be changed, tracking expiry dates and renewing on new terms.
The solution was radical: give up flexibility. They made four versions of the contract and banned any changes. Sales were told: “This is your maximum.” When everything “drifts apart”, Tony says, it’s impossible to control. Katerina agrees: if the input and output are defined, you understand every clause, while constant edits are “slippery, even dangerous”.
That, in Tony’s view, is where AI fits: a good model with RAG and a clear prompt (what to do and what not to do) should handle standard contracts.
Legal AI: faster, but confidently wrong
Hallucinations, Tony explains, are in the nature of language models: we want more from them than from a search bar, so the model adds “a dash of fantasy”. That’s why the output has to be checked. “Good news for lawyers: nobody is firing them yet.”
The riskiest area is case law. Tony asks a model about a specific case, gets a coherent story, checks it, and the case turns out to be about something else entirely. “It just made it all up, even though it’s a precise, concrete thing.” His estimate: without context a model catches about 80%, but the remaining 20% is exactly what companies pay lawyers for. Not insurance against everything, but “being able to sleep at night”.
On tools, the two disagree:
- Tony uses ChatGPT a lot and sees little difference from Claude. He likes that ChatGPT suggests the next step; he accepts about 70% of its suggestions.
- Katerina thinks Codex is currently better than Claude, because Claude more often does “something slightly different” from what was asked.
- Harvey AI is a much-hyped Legal AI. According to Tony, it is built on ChatGPT with a large prompt and a legal knowledge base, focuses on US law and is not accepting new users. Access reportedly costs around $30,000 a year. This is Tony’s account; we have not verified it.
Why English law is more precise than it looks
Tony’s surprising claim: Anglo-American law is more certain than German, Spanish or Russian law. Continental law gives you a code article that “you can read this way or that way”, and a lawyer will say “it could be this, or it could be that”. English law has thousands of precedents, not because the law is badly written, but because they capture nuance. In them you can find how a case like yours was resolved. The downside: the system is harder to learn, and precedents are exactly what models read worst.
For Cyprus this isn’t theory. According to Tony, English law works here and investment agreements can be made under it, which is one reason Cyprus is convenient for startups.
Cyprus for founders: what Tony says and what the law says
Tony lived in Cyprus for about a year and a half. In his words, Cyprus used to be an offshore zone and no longer counts as one, because taxes here aren’t zero as in the Cayman Islands. He then mentions several rates. We checked them against the 2026 law:
| # | What Tony says | What the law says now |
|---|---|---|
| 1 | Corporate tax “became 15%, I think” | Correct: 15% from 2026, up from 12.5% |
| 2 | IP Box “two and a half” | Outdated: 80% of qualifying IP profit is deducted; at 15% that gives about 3% on that profit, not on all income |
| 3 | Employees: progressive, “above 20,000”, top rate 35% | The tax-free band is now €22,000, then 20%, 25%, 30%; 35% on income above €72,000 |
| 4 | “Plus social insurance” | Yes: employees pay 8.8% social insurance and 2.65% GeSY |
| 5 | “There’s no capital gains tax here” | Nearly: true for shares, not for property (see below) |
Details, deductions and transition rules are in our guides Cyprus tax reform 2026 and Cyprus taxes: income tax, GeSY and deductions. How to set up a company: Company registration in Cyprus.
Capital gains: how founders really make money
Tony’s main point: startup founders don’t make money on revenue. Revenue is “a bonus prize”: you pay tax, keep the profit, put it back into the company or “buy yourself a Ferrari”. The real money is the increase in the value of the stake, the capital gain.
How the “flywheel” works, according to Tony:
- The company grows; an army of salespeople drives revenue.
- The valuation is calculated from EBITDA times a multiple. In hot sectors such as AI, the multiple can reach ×10.
- Venture funds care less about the entry valuation than about growth. In two years they may exit with ×5. Some companies fail, but successful deals at ×3–5 cover the losses.
- Founders start with 100% of the company and sell it piece by piece in each round. “Investors put money in, founders take money out”, based on a valuation that exists “only in people’s heads”.
And this, Tony says, is where Cyprus stands out: the gain from selling your stake is taxed at 0%, while “in almost every European country you’ll have capital gains tax”.
How the law works
Tony is right for a typical startup, with an important caveat:
- Shares and other securities. Section 8(22) of the Income Tax Law exempts “profit from the disposal of securities”. The law defines securities as shares, bonds and other titles of companies, Cypriot or foreign, and rights over them. Selling a stake in a tech company in a funding round or at exit falls under this.
- Property is the exception. The Capital Gains Tax Law charges 20% on gains from selling immovable property in Cyprus and shares in companies that own it. For indirect holdings there is a threshold: at least 20% of the shares’ market value must come from Cyprus property. Details: Property taxes in Cyprus: VAT and CGT.
- Dividends are not capital gains. If company profit is paid out to you as dividends, domiciled tax residents pay 5% SDC, or 17% on dividends from profits earned up to 2025. Qualifying non-doms are exempt from SDC. Conditions and the 60-day rule: Non-dom status in Cyprus.
- Residence. All this applies if you are a Cyprus tax resident. The country you moved from may tax the gain when you leave; Germany, for example, has an exit tax (Wegzugsbesteuerung). Check both countries before you sell a stake, not after.
Stock options and IPOs: a carrot that may never ripen
The last big topic is stock options. Tony calls them “a psychological trap”: a carrot is dangled in front of you, so you put up with things you don’t like. Getting money out of an option takes about five years. Then the shares may be locked until an IPO, and the IPO may never happen: many founders like their company being private and fully theirs. The investors are sitting and waiting too.
Katerina admits her current company promises tokens or options after a year, but her salary is fine, so she doesn’t worry about it. Tony’s conclusion: “Don’t wait, don’t cling, don’t hope; live your life anyway.”
What changed for stock options in Cyprus
Since 2026 the law has a reduced 8% rate on income from employee options and shares (section 20Δ). The main conditions:
- the Tax Commissioner approves the plan;
- vesting of at least three years, and the shares or options can’t be transferred before vesting ends;
- an exercise price of at least 50% of market value at the approval date;
- limits of twice the annual salary from the same employer and €1,000,000 over a rolling ten years; anything above is taxed as ordinary income.
If you’re promised options, ask your employer whether the plan is approved under section 20Δ. Details: Cyprus tax reform 2026.
Money, stress and nature
Another observation from Tony: the richest people in his venture-investor circle are “terribly nervous” people with difficult personal stories. His prescription: good psychotherapists. And he ends with what he loves about Cyprus: the nature and the mountains.
Chapters
00:00— Tony Maysky: law, tax, AML and disputes00:13— An important disclaimer00:45— Sumsub, KYC and legal work in Cyprus01:35— Point.Legal and legal services for companies02:37— Contract management: why contracts become a bottleneck05:11— AI, RAG and context: where LLMs help lawyers06:53— ChatGPT, Claude and Codex in everyday work07:49— Harvey AI and Legal Tech for lawyers09:27— English law, common law and trust in legal answers13:00— Cyprus: taxes, companies and the IP Box19:02— Money, stress and entrepreneurs19:44— Stock options, IPOs and why not to live in expectation21:33— Cyprus as a place to live
Frequently asked questions
Is there capital gains tax in Cyprus?
Yes, but it is narrow. The 20% capital gains tax covers Cyprus immovable property and shares in companies that own it. Gains from disposing of securities (shares, bonds and rights over them) are exempt from income tax under section 8(22) of the Income Tax Law. So selling a stake in an ordinary tech startup is generally not taxed for a Cyprus tax resident.
What is the corporate tax rate in Cyprus in 2026?
15% from 2026, up from 12.5%. Under the IP Box, 80% of qualifying IP profit is deducted, which gives an effective rate of about 3% on that profit, not on all company income.
How are employee stock options taxed in Cyprus?
Since 2026 there is a reduced 8% rate for plans approved by the Tax Commissioner: vesting of at least three years, an exercise price of at least 50% of market value, and limits of twice the annual salary from the same employer and €1,000,000 over ten years. The rest is taxed as ordinary income.
Can I use the episode as tax or legal instructions?
No. The episode is not legal, tax or financial advice. Before making decisions, check the current rules with a specialist for your situation.
Sources
- Video and subtitles — YouTube, 2026-05-29. The episode is in Russian.
- Income Tax Law 118(I)/2002, consolidated text: 15% rate, section 8(22), section 20Δ (checked 18 October 2026).
- Capital Gains Tax Law 52/1980, consolidated text.
- Cyprus Ministry of Finance: tax incentives, IP.
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