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046

Case 046Concentrated positions and liquidity eventsHard

A founder receives Rs 45 crore in a secondary sale and spends Rs 1.2 crore a year. Build the first-year plan: tax provision, a two-year cash reserve, and a staged deployment of the rest.

1The situation

Nisha Varadarajan co-founded an invented software company in Bengaluru and has just sold part of her stake to a growth investor for Rs 45 crore. Her cost for those shares was about Rs 50 lakh. She still owns shares in the company valued at around Rs 60 crore on paper, which cannot be sold for now. She spends about Rs 1.2 crore a year and has never managed money of this size.

Use an illustrative all-in tax rate of 15% on the gain, covering the tax on unlisted shares plus surcharge and cess; the actual rate, and when advance tax falls due, must be confirmed with her tax adviser.

2Your task

Build the first-year plan in order: what is set aside for tax, what is held as a spending reserve, how the rest is split and how fast it is deployed.

Quick check

Roughly how much of the Rs 45 crore is actually free to invest for the long term?

Worked solution

Try it on paper, then open one step at a time.

30-second answerThe answer to give first

Provision first, reserve second, then deploy: set aside about Rs 6.67 crore for tax and Rs 2.4 crore for two years of spending, leaving Rs 35.92 crore to invest. Put 40% into a debt ladder at once, stage the 50% equity over 12 months at about Rs 1.50 crore a month, and commit the 10% for alternatives over three years. Her spending is about 3.3% of the pool, which the debt ladder can refill.

Step 1Why does tax come before anything else?

A shopkeeper who spends the GST he has collected before paying it has spent money that was never his. Part of the Rs 45 crore belongs to the tax authority, and investing it in equity risks having to sell after a fall to pay a fixed bill. On a Rs 44.5 crore gain at an illustrative 15%, that is about Rs 6.67 crore, held in a liquid fund or short deposits timed to the advance taxTax paid in instalments during the year in which income or gains arise, rather than all at once after the year ends. dates her adviser confirms.

Step 2How big should the reserve be, and why two years?

Two years of spending, Rs 2.4 crore, in short debt and deposits. The reserve lets her live through a two-year equity slump without selling anything, which is what keeps the rest of the plan intact. It also buys time. People who come into sudden money often make their worst decisions in the first months, so a rule of no large commitments for three to six months belongs in the plan too.

Provision, reserve, then deploy, Rs crore45.0Proceedssecondary sale-6.67Tax provisionillustrative 15%-2.4Cash reserve2 years' spending35.92To investthe poolThe pool, by sleeveDebt ladder, 40%Rs 14.37 cr, month 1Equity, 50%Rs 17.96 cr, 12 monthly stepsAlternatives, 10%Rs 3.59 cr, over 3 years
Rs 45 crore of proceeds less a Rs 6.67 crore tax provision and a Rs 2.4 crore two-year reserve leaves Rs 35.92 crore to invest, split 40% debt, 50% equity and 10% alternatives.
Step 3How is the pool split, given the stake she still holds?

Nisha still has about Rs 60 crore on paper in one unlisted software company, which is already a large, risky, illiquid bet. So the liquid pool should diversify away from that bet: a meaningful debt share, listed equity spread across sectors rather than tilted to technology, and a small alternatives sleeve with a hard cap on new startup investments. A 40/50/10 split does that: Rs 14.37 crore in a laddered bond and deposit book maturing over one to five years, Rs 17.96 crore in diversified equity, and Rs 3.59 crore for alternatives.

Step 4How fast should the money go in?

Each sleeve at its own pace. The debt ladder goes in during the first month, since there is little to gain by waiting; equity goes in through 12 monthly transfers of about Rs 1.50 crore; alternatives are committed across three yearly vintages and drawn by the funds over time. Her yearly spending of Rs 1.2 crore is about 3.3% of the pool, and each year's maturing rung of the ladder refills the reserve, so she never has to sell equity to live.

How the Rs 35.9 crore pool moves from cash into the plan102030Rs croreM0M6M12M18M24Months after the money arrivesdebt ladderequityalternativeswaiting in a liquid fund
The Rs 35.92 crore pool moves from a liquid fund into the plan at three speeds: the debt ladder in month 1, equity in 12 monthly steps of Rs 1.50 crore, and alternatives drawn gradually over three years.

Close with the limit. The split and the pace are judgements for this client, not rules; a founder with no remaining stake could hold more equity. What does not change is the order: provision, reserve, then deploy. Every other choice can be adjusted later without harm; getting the order wrong can force a sale at the worst time.

Where candidates lose it

Candidates jump straight to an asset allocation for Rs 45 crore. They have invested the tax and ignored the spending, so the first equity fall could force a sale to pay the tax authority.

The second miss is ignoring the Rs 60 crore still held in the company. A plan that adds technology funds and startup deals to a founder already heavy in one startup has doubled the concentration it should reduce.

What the interviewer asks next

  • Nisha wants to write angel cheques to other founders. How much, and under what rules?
  • The unlisted stake doubles in value on paper. Does the plan change?
  • How would you design the debt ladder so that each year's rung refills the reserve?
← Case 045A client sells a property with a Rs 3 crore long-term gain. Compare buying another house, buying specified exemption bonds with a lock-in, and paying the tax and investing freely, on after-tax wealth over five years.Case 047 →A resident Indian holds Rs 5 crore of US-listed shares directly. Explain her US estate tax exposure and compare holding the same exposure through an Indian fund.

Company names and figures are illustrative.

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