Taxes when selling an online business: what to ask your advisor

Short answer. How much tax you pay when selling an online business depends on your country, whether you sell shares or assets, how the price is allocated, when you're paid and which reliefs apply. This isn't tax advice: it's the list of questions to take to your advisor before you sign a letter of intent, because the structure is hard to change afterwards.

Key takeaways

• Talk to a tax advisor before the letter of intent, not after the contract.
• Share sale or asset sale is often the biggest tax decision in the deal.
• How the price is split across assets can change what you owe.
• Being paid over time, or partly on results, can change when you're taxed.
• Reliefs and rates change. Check the rules that apply on your expected closing date.

Why does tax planning need to start early?

Because the decisions that drive your tax bill are made early, in the letter of intent: what's being sold, by whom, for how much, and when it's paid. By the time lawyers draft the purchase agreement, those choices are hard to undo without reopening the price.

A short meeting with your advisor before you go to market costs little. Discovering after signing that a different structure would have left you more money costs a lot.

This article isn't tax advice. It's a list of questions, with a few examples of how rules work in specific countries, so you can have a better conversation with someone qualified in yours.

Question 1: who is the seller, me or my company?

If your business sits in a company, you can sell the company's shares (a share sale) or the company can sell the business's assets (an asset sale). The tax consequences are different:

• In a share sale, you personally sell your shares, and the gain is generally taxed under the rules for disposing of shares in your country.
• In an asset sale, the company sells the assets and is taxed on its gain. Getting the money from the company to you can then be a second taxable step, depending on how you do it.

Some countries offer reliefs for selling shares in a trading company. In the UK, for example, Business Asset Disposal Relief applies an 18% rate to qualifying gains on disposals on or after 6 April 2026, up to a £1 million lifetime limit (GOV.UK, HS275). Conditions apply, and other countries have different regimes.

Ask: Which structure works better for me, and is the buyer likely to accept it? Our comparison of asset sale vs share sale covers the non-tax side.

Question 2: how will the price be allocated?

In an asset sale, the price is split across what's being sold: inventory, equipment, intellectual property, goodwill and so on. Different assets can be taxed differently.

In the US, buyer and seller both report the allocation on Form 8594 when a group of assets making up a business is sold (IRS, About Form 8594). The buyer and seller often want different splits, because what lowers tax for one can raise it for the other.

Ask: How should the price be split, and what do we agree with the buyer in the contract?

Question 3: what if I'm paid over time?

Part of the price paid later, as seller financing or as an earn-out, can change when the gain is taxed.

In the US, a sale where at least one payment is received after the tax year of the sale is generally an installment sale, and the regular sale of inventory doesn't qualify for that treatment (IRS Publication 537). Earn-outs raise their own questions: whether the future amount is taxed at closing or when received, and what happens if it's never paid.

Ask: When will I be taxed on deferred and conditional payments, and what happens if they're reduced or not paid?

Question 4: is VAT or sales tax due on the sale?

Selling a whole business can sometimes fall outside VAT. In the UK, HMRC says that if you sell assets as part of a business that's a going concern then, subject to conditions, no supply takes place for VAT purposes (GOV.UK, VAT Notice 700/9). EU countries have their own versions of this rule. If the conditions aren't met, VAT may be due on the assets.

Ask: Does my sale qualify, and what do we need to do to make sure?

Question 5: where am I tax resident, and where is the company?

Cross-border situations are common in eCommerce: a founder in one country, a company in another, a buyer in a third. Residency affects which country taxes your gain and how.

Moving residence shortly before a sale is complex and often scrutinised. Don't plan it without specialist advice.

Ask: Which countries can tax this sale, and are there treaties or reliefs that apply?

Question 6: does timing matter?

Rates and reliefs change. The UK Business Asset Disposal Relief rate, for instance, was 10% for disposals up to 5 April 2025, 14% from 6 April 2025 and 18% from 6 April 2026, according to HMRC's helpsheet (GOV.UK, HS275). The end of a tax year can also change when the gain falls.

You can't always control when a deal closes, but you can know whether a date matters for you.

Ask: Is there a date before or after which closing changes what I owe?

Question 7: what happens to the money left in the company?

If the business sits in a company with cash, inventory or receivables, decide what happens to them. In a share sale, the price is often adjusted for cash and debt. In an asset sale, cash stays in your company and needs to be extracted.

Ask: What's the most efficient way to take cash out of the company before or after the sale?

Question 8: what can I do now to be ready?

• Keep clean, separate business accounts and a monthly P&L. Your advisor needs good numbers too.
• Gather company documents, past tax returns and VAT filings.
• Write down how you took money out of the business in past years.
• List the deal options you're considering: share or asset sale, payment at closing or over time.

Which advisor do I need?

For most founders, three people cover it:

Sometimes one firm covers two of the roles. What matters is that the tax advisor sees the deal structure before you agree it, and that the lawyer knows what the tax advisor recommended.

If you're in one country and the buyer is in another, ask whether your advisor has handled cross-border sales before, or works with someone who has.

How WiseExit works with your advisors

We don't give tax or legal advice. We do help you bring the right questions to your advisors at the right moment, before terms are agreed, and we work alongside them on the structure of the deal.

The first step is knowing what the business is worth. Request a free valuation: answer in 24 hours, zero upfront costs, no commitment to sell.