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FOUNDER PLAYBOOKMarch 20257 min read

Stop Optimising for Tax. Start Optimising for Valuation.

CA Ankit Gupta
Led by CA Ankit GuptaFounding Partner, Asquare Consulting Group

"Most Indian founders have spent years minimising their tax liability. That is rational. It is also, at the moment of a fundraise or exit, one of the most expensive decisions they ever made."

There is a version of your business that pays almost no tax. And there is a version of your business that gets a good valuation. In most cases, they are not the same version.

This is the central tension that almost no founder thinks about until an investor is sitting across the table, looking at five years of books, trying to figure out what this business actually earns.

What Tax Optimisation Actually Does to Your Books

When you run a business primarily to minimise tax, the signals you send to an investor are almost uniformly negative. Promoter salary is suppressed, which means EBITDA looks artificially high. Expenses are inflated, which means margins look compressed. Related-party transactions are used to shift income, which means revenue concentration looks different than it is.

None of this is necessarily illegal. Most of it is standard practice in Indian MSMEs. But every single one of these adjustments is something an investor will normalise out of your financials before they offer you a number. And the number they arrive at after normalisation is almost always lower than the number you expected.

The Normalisation Problem

Investors and acquirers do not value your business on the numbers you report. They value it on normalised numbers: what the business would look like if it were run at arm's length, with market-rate salaries, no related-party distortions, and no expense line items that belong to someone’s personal life.

The gap between reported financials and normalised financials is where most valuation negotiations happen. The wider that gap, the more uncomfortable the conversation. And the more your books have been optimised for tax, the wider that gap tends to be.

"An investor does not care what you paid in tax last year. They care what this business will earn under their ownership. Those are two very different questions."

What Valuation-Ready Books Actually Look Like

A business that is being prepared for investment or exit needs to demonstrate sustainable, arm’s-length earnings. That means promoter compensation at market rates. It means expense lines that reflect the actual cost of running the business, not the personal expenses of its owners. It means related-party transactions that are disclosed, documented, and defensible.

None of this means paying more tax than you need to. It means understanding that the same financial decisions that minimise your tax today will reduce your valuation tomorrow, and making those trade-offs consciously, not by default.

The Conversation Most Founders Have Too Late

We see this consistently: a founder reaches a term sheet, the investor’s team begins normalising the financials, and the valuation walkdown begins. Three years of tax-optimised books, compressed on paper, get unwound item by item. The founder is surprised. The investor is not.

The time to think about this is not when the term sheet arrives. It is two to three years before you plan to raise, when there is still time to restructure how your business presents itself on paper, without changing how it actually operates.

Related Topics#Valuation#TaxOptimisation#FounderPlaybook#Financials
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