Business
Investment Regrets: Experts Reflect on Missed Opportunities

Investment professionals often have their own regrets about missed opportunities in the market. From tech giants to cryptocurrencies, many experts reflect on how different their financial landscapes might look had they made different choices.
Big Missed Opportunities in Tech and Crypto
The story of missed investments often begins with technology. According to Jeremy Sullivan, an investment advisor at Hamilton Hindin Greene, a $10,000 investment in Amazon at its initial public offering in 2007 would now be worth nearly $30 million. This staggering figure comes despite the company’s share price experiencing volatility, notably during the ‘Dot Com’ crash when it dropped over 90 percent.
Similarly, Greg Smith, head of retail at Devon Funds Management, points to Amazon’s early trading price of just US$0.07 in May 1997, highlighting the missed potential as its shares now exceed US$220.
The cryptocurrency market, particularly Bitcoin, represents another area of significant regret for many. Jason Titman, chief executive of Swyftx, noted that a consistent investment of $10 per day for ten years would yield a portfolio worth approximately $2.8 million today. Smith recalls a missed opportunity in 2013 when Bitcoin traded at $1,000, a time when he was encouraged to invest but chose not to.
The tech sector also includes companies like A2 Milk, which Smith wishes he had invested in when shares were just $0.02 in 2004. The share price peaked above $20 in 2020 and currently sits around $8.60.
Real Estate and Unique Finds
Real estate investment coach Steve Goodey emphasizes the wealth generated from property investments over the past decade. He notes that the median house price in New Zealand has soared from approximately $170,000 in 2000 to nearly $800,000 today. Goodey suggests that owning land in Auckland a decade ago would have been a lucrative investment.
In a more personal reflection, Dean Anderson, founder of Kernel, shares a nostalgic regret about a 1967 Land Rover he purchased during university for $1,800. Although he made a profit by selling it later, he estimates its current value could be thirty times that amount, not to mention the cherished memories associated with it.
Other experts highlight a blend of past regrets and lessons learned. Brad Olsen, chief executive of Infometrics, recalls not investing in Facebook when shares were priced at around $20 in 2012, now worth over $770. He reflects on the countless missed investments, including properties, but maintains satisfaction with his risk tolerance over the years.
Lessons Learned and Looking Forward
In a broader context, Shamubeel Eaqub, chief economist at Simplicity, points out his own investment missteps, including a failed venture with a start-up. Eaqub emphasizes the importance of focusing on consistent savings and diversified portfolios rather than fixating on specific missed opportunities.
The stories shared by these investment professionals serve as reminders that while some opportunities slip away, the market is dynamic, and future prospects remain. As they continue to navigate their investments, the lessons learned from the past will undoubtedly shape their strategies moving forward.
Engaging in regular savings and understanding the power of compounding can lead to more substantial gains in the long run. As the investment landscape evolves, those reflections on missed opportunities may inspire more informed decisions in the years to come.
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