The Biggest Investment Risks Are the Ones You Don’t See Coming

Risk: Where You Least Expect It

June 12, 2026

Iceberg with most of its mass hidden beneath the water, representing unseen investment risks.

Risk: Where You Least Expect It

June 12, 2026

By Rick Waechter, Founder

Some of the greatest fortunes have been created by correctly forecasting where risk will rear its ugly head. Michael Lewis, in The Big Short, made famous the story of a few investors who saw the mortgage crisis coming in 2007-2008, bet against mortgage bonds, and pocketed tens or hundreds of millions of dollars. These kinds of stories, while wonderfully entertaining, mislead you. History is written by the victors. Most people who forecast risk get it wrong – and of course those stories typically don’t become best-selling books or popular films.

I have plenty of experience misjudging where risk will appear. Over decades, I have learned that the biggest risks come out of nowhere. My solution: don’t waste time predicting. Spend your time (and money) diversifying. That way, wherever risk comes from, you won’t be too exposed.

Here’s a story from my previous career in which a lot of smart, hardworking people spent hundreds of hours analyzing and protecting against various risks … and got it totally wrong.

I spent 20+ years as a Wall Street investment banker (cue the well-earned derision). One of the projects I remember most involved raising almost $2 billion for the government-owned telephone company in Indonesia, by listing their shares on the New York Stock Exchange and selling them to investors around the word.

The drill:

  • To determine the appropriate share price, dozens of bankers made detailed calculations of future growth in revenue and expenses.
  • We spent inordinate time understanding risks such as inflation, recession, regulatory changes, competition, new technology and the challenges of moving from a government-owned company to a market-facing company.
  • We then created a detailed financial model to incorporate every key variable, and to run all kinds of sensitivity analyses.

Much of the analysis was solid – or would have been solid. Except for one, ahem, small thing we missed. The Indonesian currency, which had steadily and predictably depreciated gradually against the US dollar for decades, collapsed about two years after the shares were listed. The currency fell by 75%+ in a year. The shares became almost worthless to US dollar-based investors.

We had considered all kinds of risks, and – working with the Indonesian government – we had agreed to protections like a strong regulatory regime.

But we flat-out missed the risk which mattered most.

Many investors today are worried that a bursting “AI bubble” may cause high-flying U.S. tech stocks to drop, potentially sharply. It may. But if you want to protect yourself against that risk, don’t do it by taking on another big risk – buying gold, or Bitcoin, or junk bonds, or art, or your next-door neighbor’s can’t-lose deal. The only reliable way to protect yourself as an investor is by diversifying across geographies, sectors, and company sizes within stocks, high-quality bonds, and potentially real estate or reputable private investments.

None of knows where the next risk will come from. Take it from me. I’ve made that mistake one too many times.

(PS – the Indonesian telephone company’s stock rebounded strongly after a few years, if any investor had the nerve to hold on. I suspect few did.)

Related Blog Posts

Layered rock strata representing the long-term perspective and historical trends that shape investing.
Zooming Way, Way Out on Economic Data
By Justin May, Portfolio Manager 2026 marks 100 years of the S&P 500. The index has returned over 10% annually ...
More
Soccer ball on the field before a World Cup-style match, illustrating investing lessons about patience, diversification, and market efficiency.
Investing Lessons from the World Cup
By Rick Waechter, Founder The World Cup just concluded. It was another spectacular tournament. The only thing that is more ...
More
Stack of gold bars representing investing in gold as a long-term investment.
Gold Glitters, and Then It Doesn’t
By Rick Waechter, Founder Occasionally, clients will ask if they should own gold. Because the price almost doubled in 2025, ...
More
Gift box with cash representing the free $1,000 available through Trump accounts.
Trump Accounts: Take the $1,000, But Don’t Add More
By Rick Waechter, Founder Trump accounts just launched. They are investment accounts for kids under 18, designed to be used ...
More

This article is not intended to provide tax, legal, accounting, financial, or professional advice. Readers should seek advice from qualified professionals who can review their specific circumstances. Old Peak Finance endeavors to provide information that is accurate and current. However, we cannot guarantee that this information has not been outdated or otherwise rendered incorrect by new research, legislation, or other changes. Old Peak Finance has no liability or responsibility to any individual or entity with respect to losses or damages caused or alleged to be caused, directly or indirectly, by the information contained on this website.

Have Questions?

Sign up for a complimentary call. We'll listen and determine together if we can help you achieve your goals.

Newsletter Sign Up

Something went wrong. Please check your entries and try again.
Scroll to Top