Imagine watching a stock you knew intimately skyrocket, leaving you on the sidelines. Or selling a winner too early, only to see it climb to unimaginable heights. That's the painful reality faced by even the most seasoned investors. At the launch of the MOSL Wealth Creation Study, legendary investors Raamdeo Agrawal, Ramesh Damani, and Sunil Mahatani shared their biggest investment regrets, offering invaluable lessons on conviction, patience, and the magic of compounding – insights that could dramatically reshape your investment strategy.
Ramesh Damani, a market veteran, candidly admitted his blunder with Bajaj Finance. Despite understanding the company and admiring its leadership, he missed the boat when it was listed. "My circle of confidence was in my backyard, and yet for some reason, I missed out... it was extraordinarily stupid of me… I know the hurt of missing a stock like that," he confessed. This highlights a crucial point: familiarity doesn't always translate to action. Sometimes, the best opportunities are right under our noses, but we fail to recognize them.
Damani also recounted his experience with Apollo Hospitals. He initially bought the stock at a mere Rs 20 in 1993. Over the next 25 years, it exploded in value, increasing 100-fold! But here's where it gets controversial... He sold during the COVID downturn at Rs 2,000. His reason? "I sold because I had made too much money, not because the fundamentals had changed." Damani himself acknowledged the gravity of his mistake: "If you want to be Warren Buffett, you cannot make mistakes like that. Those are unacceptable mistakes.” This illustrates the danger of letting emotions, specifically greed or fear of losing gains, override rational analysis. Selling a fundamentally strong company simply because you’ve made a significant profit is a classic error. Have you ever made a similar mistake?
Sunil Mahatani, Owner and CIO at Kingfisher Investors, echoed this sentiment with his Apple Inc. experience. Recognizing the shift from a high-tech company to a consumer-focused business after Steve Jobs's return and the launch of the iPod in 2001, Mahatani sold after the stock doubled. And this is the part most people miss... He missed out on the astronomical gains that followed, transforming Apple from a $4 billion market cap company to a behemoth worth over $4 trillion. "The opportunity got away simply because I thought there were cheaper opportunities elsewhere," he explained. This underscores the importance of assessing the long-term potential of a company, rather than chasing short-term gains in seemingly undervalued alternatives.
But Mahatani's biggest regret wasn't a tech giant; it was HDFC in 1989. During a visit to India from the US, he discovered the company and was struck by its value. "One that I didn’t buy, even though it looked absurdly cheap, was HDFC," he said. "It was at around Rs 190, earning Rs 65 a share and paying an Rs 18 dividend. You were getting nearly 10%. And it had been compounding at 25% a year with a 25% ROE.” Despite recognizing the incredible opportunity, he didn't have capital in India at the time. He even urged his father to invest, but to no avail. "Instead of spending money on a plane ticket, I should have just bought the stock," he quipped. This highlights the importance of seizing opportunities when they arise, even if it requires unconventional measures. It also shows how sometimes, external factors can prevent us from capitalizing on even the most obvious investment opportunities.
Raamdeo Agrawal, co-founder of Motilal Oswal, shared his early experience with HDFC Bank. In 1995, he bought shares at Rs 40, believing private banks would outperform PSUs. "I saw the HSBC building in Hong Kong, and I thought, our HSBC is going to be HDFC," he said. However, shortly after buying, negative news about one of HDFC’s partner banks prompted him to sell at Rs 52.50. The stock never dropped below that price again. "The lesson was simple: you have to stay with your conviction," he emphasized. This underscores the importance of thorough research and unwavering belief in your investment thesis, even in the face of short-term market fluctuations or negative news.
Agrawal also reflected on Bharti Airtel, which he bought in 2003 at Rs 25 per share, facing skepticism from his peers. Within a week, the price surged to Rs 33–35, and he sold a portion of his holdings. However, he maintained a stake as the stock soared to Rs 1,180, eventually selling when the 2G telecom scandal caused a temporary dip. Today, Bharti is a major wealth creator in India. "When a business gains momentum and tailwinds, it can become a wealth-generating machine if you stay invested," he stated. This emphasizes the potential rewards of patiently holding onto high-growth companies, allowing compounding to work its magic over the long term.
Highlighting the rarity of genuine compounders, Agrawal noted that in the Motilal Oswal Wealth Creation Report, “Of the starting list of top 500 companies in 2008, only 35—just 7%—ended up as compounders. Their average price CAGR over 2008–2025 is a handsome 23%. The rare winners combine sustained growth, consistent outperformance, and strong leadership.” This stark statistic underscores the difficulty of identifying and holding onto truly exceptional companies. It's not just about finding a good company; it's about finding a company that can consistently deliver exceptional results over many years.
These stories from investment giants offer a powerful reminder that even the best miss opportunities and make mistakes. The key is to learn from those experiences, develop strong conviction, practice patience, and understand the transformative power of compounding. What are your biggest investment regrets, and what lessons have you learned from them? Share your thoughts in the comments below!
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