← Back to Curriculum

Intermediate

Case Study: A Failed Angel Bet, Lessons From a Startup Shutdown

An intermediate case study that starts where most startup stories end. A Pune-based angel investor puts ten lakh rupees into a B2B ordering app for kirana stores at its seed round, follows on in a bridge round, and then lives through the shutdown. Each chapter works through one stage with real numbers: the original CCPS terms and liquidation preference, the unit economics that never closed, the failed fundraise and the acqui-hire offer, how Indian companies actually close (strike-off, voluntary liquidation and the payout waterfall), what the angel recovered down to the rupee, how the capital loss is treated for tax, and what the loss means for an angel portfolio built on power-law returns. Built for experienced retail investors, HNIs and angels building a portfolio who want to understand the downside before they write the next cheque.

Angel InvestingStartup ShutdownsLiquidation PreferencePayout WaterfallFollow-On DecisionsCapital Loss Tax TreatmentPower Law Portfolios

MODULES

5

DURATION

~3 hrs

TRACK

Alternative Investing

What You'll Master

Read a seed-round CCPS deal for the terms that decide what you get back in a shutdown, not in a success

Diagnose broken unit economics from contribution margin, burn multiple and runway before the founders admit it

Decide whether to follow on in a bridge round, and recognise when pro rata rights become a trap

Understand how Indian startups actually close: strike-off, voluntary liquidation and the order in which claims get paid

Calculate an angel's recovery from an acqui-hire or asset sale using the liquidation preference waterfall

Handle the aftermath: documenting the loss, its capital loss tax treatment, and carry-forward

Size angel cheques so that a shutdown is an expected cost of the strategy, not a portfolio disaster

Access Level

LEARNER

Start Learning Now →Sign in to resume

Everything included

Full Text Playbooks

Actionable Exercises

Mobile Reading Mode

Lifetime Updates

Curriculum Breakdown

Chapter 1: The Bet

3 Lessons

Why Study a Shutdown Instead of a Success10 min read

Meet the Investor and the Startup: A Ten Lakh Cheque Into a Kirana Ordering App12 min read

Reading the Original Deal: CCPS, Valuation and the Liquidation Preference14 min read

Chapter 2: The Slide

3 Lessons

Unit Economics That Never Closed: Contribution Margin and the Burn Multiple14 min read

The Bridge Round: Following On and the Pro Rata Trap13 min read

The Last Twelve Months: Runway, a Failed Fundraise and the Acqui-Hire Offer13 min read

Chapter 3: The Shutdown

3 Lessons

How Indian Startups Actually Close: Strike-Off, Voluntary Liquidation and the Board Decision14 min read

The Payout Waterfall: Who Gets Paid First When a Company Winds Up14 min read

Running the Numbers: What the Angel Actually Recovered13 min read

Chapter 4: After the Loss

2 Lessons

Booking the Loss: Capital Loss Treatment, Set-Off and Carry-Forward13 min read

The Paper Trail: Documents Every Angel Should Keep From Day One11 min read

Chapter 5: Lessons for the Portfolio

3 Lessons

Sunk Cost and Escalation: The Behavioural Mistakes in This Case12 min read

Power Law Maths: Why One Shutdown Does Not Make a Bad Strategy13 min read

Capstone: Run Your Own Shutdown Post-Mortem14 min read