Monday, February 16, 2026

The Biggest Risk Is What You Can't See Coming

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The Biggest Risk Is What You Can't See Coming

Alexander Green, Chief Investment Strategist, The Oxford Club

Alexander Green

Investors everywhere are looking for the same thing... a "sure thing"

Or, at least, something that has such a high probability of a big payoff that it's virtually a sure thing.

In a world of constant change and "creative destruction," however, that goal will remain forever elusive.

Let me give you an example from my formative years...

In the mid-1980s - as a young man fresh out of college - I was looking for an investment idea, something with almost a 100% chance of paying off.

And a friend had just the ticket, he said: pay phones, the ultimate utility.

They were everywhere - train stations, hotel lobbies, gas stations, busy street corners.

Calling was still a tethered experience, and hard currency was the lifeblood of communication on the go.

An investor could hardly imagine a world without them.

In fact, small entrepreneurs often bought routes of pay phones - hundreds of metal boxes bolted to walls and kiosks - each one dropping coins like a miniature cash register that never closed.

The model was deceptively simple and beautifully consistent.

Once you secured a good location - a busy intersection, a bar, a hospital waiting area - the cash just rolled in.

Operators paid a commission to the property owner, covered maintenance, and collected buckets of coins every week.

It was steady, tangible income.

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Investment newsletters at the time touted pay phone routes as the kind of boring, inflation-resistant business that quietly made millionaires.

There were franchises, limited partnerships, even ads in the back of Business Week and Barron's promising "8-12% annual cash returns, backed by real metal"

The returns seemed almost unstoppable. Long-distance carriers and coin rates kept rising. And so did profits.

The barrier to entry was physical - no "disruption" could happen without someone literally ripping phones off walls.

(Or so we thought.)

To many small investors, a pay phone was like owning a vending machine for necessity rather than indulgence.

People could live without a Coke. They couldn't live without making that call home or to the office.

You know where this is going...

Cell phones started appearing - chunky status symbols at first, then smaller, cheaper, and suddenly everywhere.

By the mid-1990s, the number of calls made from pay phones dropped off a cliff.

Phone companies began decommissioning entire routes, and independent operators watched collections shrink from overflowing to nearly empty.

The franchise ads vanished from magazines, replaced by pages selling the next wave of "can't-miss" investments - internet startups.

By the 2000s, the once-proud pay phone was reduced to an urban relic.

Investors who had made small fortunes were left with piles of obsolete equipment, much of it sold for scrap or nostalgia value.

The idea that a pay phone was a permanent fixture turned out to be a mirage - an early lesson in how quickly technology can vaporize what once seemed indispensable.

Looking back, the story of the pay phone isn't just about technology or business. It's about conviction.

Every generation has its "sure things" - tangible, comforting investments that feel protected from change.

But permanence, as the pay phone proved, is an illusion in our world of innovation and progress.

The investment takeaway?

It's not wrong to give up seeking consistent moneymakers. But the key is to realize that every investment carries risk.

Even U.S. Treasury securities - the safest credit on earth - subject holders to the risks of inflation and devaluation.

It's another reminder of why The Oxford Club's investment system is based on asset allocation, diversification, position sizing, and trailing stops.

These tools provide your portfolio with battle-hardened protection.

Because the biggest risk is what you can't see coming.

Good investing,

Alex

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