Why I Wrote Roots & Wings

The first stock I ever bought taught me nothing about investing and everything about myself.

It was December 1999. I was in my twenties, working out of Infosys’s client site in the San Francisco Bay Area, building internet ad-tech systems for Paramark, a startup founded by Sankrant Sanu (an IIT Kanpur whizkid who had been an early builder at Microsoft), Hitendra Wadhwa (now a professor at Columbia University), and Mike Tuchen. The mood in every office park from Palo Alto to San Jose was electric. Valuations had detached from reality, but nobody seemed to care. A colleague casually mentioned a stock that had “already doubled and was going to double again.” I bought it without reading a single page of its financials. I did not know its debt, its cash flow, or whether its management owned a single share.

The stock did go up for a few weeks. Then the dotcom bubble burst, and my position evaporated. The loss was small in absolute terms (I was a young professional and had invested only what I could afford to lose). But it exposed something no textbook had: I was flying blind, with no framework for deciding what to buy, when to buy it, or when to walk away.

Two decades and several thousand annual reports later, that moment of reckoning became a book.

The Pattern I Could Not Unsee

Over those two decades, across careers in technology, insurance, lending, and asset management, I kept seeing the same two patterns repeat. They stopped feeling like individual company failures and started feeling like a single structural insight.

The first kind of company looks impeccable on paper. The balance sheet is spotless, the promoter is honest, the governance is beyond reproach. You buy the stock feeling virtuous about your rigorous analysis. And then you wait. Five years later, the company is still earning roughly what it earned when you bought in. Your capital has been safe, yes, but it has also been imprisoned. The company had deep roots but no wings.

The second kind is intoxicating. Revenue doubles every year. The stock triples. Management talks about disruption, market expansion, a massive runway ahead. Then one bad quarter hits. A key customer defaults. A commodity price spikes. And because the company has been funding its ambitions with borrowed money and stretched payables, the whole edifice starts to crack. Within two years, the stock is down 80 per cent and you are left holding the wreckage. The company had magnificent wings but shallow roots.

Think of every spectacular corporate collapse you have witnessed in India over the last two decades. Jet Airways, Cafe Coffee Day, Satyam, DHFL, Yes Bank, Kingfisher Airlines. Strip away the individual stories and a common pattern emerges. Each company had taken on debt (or engaged in financial practices) that its foundation could not support. When the storm arrived, and the storm always arrives sooner or later, the roots proved too shallow.

The companies that created lasting wealth, the ones where a patient investor’s capital actually compounded into something meaningful over ten or fifteen years, were invariably the ones that had both. Strong foundations and the ability to grow. Deep roots and powerful wings.

Why Each Career Chapter Mattered

Each vantage point of my career offered an intimate view of this pattern, and contributed something specific to the framework.

At Infosys, building enterprise systems for clients across manufacturing, retail, telecom, and banking gave me a crash course in how different industries create or destroy value. The IT industry itself provided vivid examples of companies that scaled beautifully and others that scaled but imploded (Satyam being the most dramatic case).

At Northwestern Mutual in the United States, a Fortune 100 life insurer with one of the largest investment books in the industry, I got my first exposure to how a truly well-run institution manages capital across decades, not quarters. The discipline there was striking.

At ICICI Lombard, a general insurer underwrites risk across every sector of the economy, so every proposal that came to the Management Committee was a compressed case study of a company’s operations and vulnerabilities. Participating in those meetings, where credit proposals were scrutinised and portfolio risks assessed, shaped my understanding of how serious investors think.

At Poonawalla Fincorp, I saw from the lending side how companies behave when they need capital versus when they have it. The gap between reported financials and economic reality becomes starkly visible when you are the one deciding whether to lend.

These experiences, layered over years, made it clear that evaluating a company requires looking at multiple dimensions simultaneously. A single metric, whether it is PE ratio or revenue growth or return on equity, never tells the full story. You need a framework.

What the Framework Actually Is

The Roots & Wings framework evaluates companies across six dimensions, three that measure the strength of their foundations and three that measure their capacity for growth.

The Roots (what holds in a storm): balance sheet resilience, capital allocation mastery, and management quality combined with forensic health. Together, they answer one fundamental question: can this company be trusted with your capital?

The Wings (the compounding engine): consistent financial growth, market dominance, and innovation. Together, they answer a different question: can this company multiply your capital?

We have tested this framework against actual market returns using a rigorous multi-year rolling methodology. The results are in Chapter 10 of the book. One finding from that analysis may surprise you: over short periods, there is almost no measurable penalty for buying companies with weak foundations. The penalty only becomes visible at three years and devastating at five. This is why most investors never learn the lesson. By the time shallow roots reveal themselves, the capital is locked in and the opportunity cost has been paid.

What This Book Will Not Do

This book will not give you a list of stocks to buy. Stock recommendations have a shelf life measured in days; the framework has a shelf life measured in decades. It will not promise extraordinary returns or tell you when to buy. It is a structured lens for human judgement, not an algorithm.

Every chapter uses real Indian companies as case studies, not generic theory. The ABCDEF forensic checklist in Chapter 6 is a practitioner tool, not an academic exercise. The scoring methodology in Chapter 10 has been tested against actual market data. If you are looking for companies that will compound your wealth over five, ten, or twenty years, the frameworks in this book will serve you well.

The Mountain Metaphor

In October 2010, on day five of a trek to Roopkund Lake in Uttarakhand, I found myself inching across a steep snow face at close to 15,000 feet. The trail had narrowed to nothing, and the only way forward was to leap across a gap between two rocky outcrops with a sheer drop below. I planted my metal hiking stick into the snow, shifted my weight, and jumped. The stick snapped. For a sickening instant I was sliding downward with nothing to hold on to, the valley yawning beneath me. Instinct took over: I dug all four limbs and the broken remnant of the stick into the snow and managed to stop after falling about four feet.

What stayed with me long after the bruises healed was the lesson that every seasoned mountaineer already knows: focus only on the next step. Not the summit, not the distance remaining, not the drop below. Just the next foothold. It is a discipline that works because it replaces panic with process.

Trekking without proper gear and a clear-headed process is how people get hurt in the mountains. Investing without a framework is how people get hurt in the markets.

That is, in a sentence, why I wrote this book. Not to give you the next stock tip, but to hand you the gear and the process so you never have to fly blind again.

Roots & Wings launches May 2026 via Notion Press. Get notified at launch →