My grandfather’s investment philosophy was like a fax machine in the office. Humming along reliably until everyone else moved to email and forgot to tell it.

Investment thinking since his time has not changed much: age into bonds, buy household names, sleep easy. It’s the investing equivalent of driving the speed limit in the left lane. Safe, predictable, and probably going to get you there. Eventually. Maybe.

But that investing strategy isn’t always the safe bet it is cracked up to be.

General Electric was once a widow-and-orphan stock. Kodak was untouchable. Nokia owned mobile. All were retirement-portfolio staples. All proved that ‘safe’ is just a story we tell ourselves until the story changes.

The real risk isn’t volatility. It’s thinking you’ve eliminated risk entirely, or the opportunity cost of taking very low risk and missing out on possible returns.

 

Contrarians lean into discomfort

 

Building meaningful wealth means accepting an uncomfortable fact: security and opportunity exist in tension, not harmony. You can’t have one without negotiating with the other. The people who pretend otherwise are either lying or losing.

History punishes those who only ever chose comfort, but rewards those who allow in some discomfort.

Sometimes those who leaned into ridicule and held their nerve changed their financial destiny meaningfully.

Marginal differences in return may seem trivial to some. But when you consider a longer time frame, an extra 0.5% to 1% return per year may lead to a stark difference in the end wealth of your portfolio. You might look back and be grateful you decided to take a risk, contrary to mainstream advice.

And few ideas make investors more uncomfortable than the risk of investing in something that is illegal in most places…

 

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