May 26, 2020
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How Being an Alcoholic Nerdy Sneakerhead With a Weakness For Baseball Might Make You Rich

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The most unconventional successful investments

Alright, that title is all over the place, but you’ll see why in a minute. This week’s article is about the weirdest alternate investments.


Whether you buy limited-edition sneakers on release and resell them immediately for a hefty profit or just let them sit in your basement for a couple of years, sneakers can land you outlandish returns on our investment. For example, the Air Yeezy 2 “Red Octobers” sold for a retail price of $250 in 2014 and are now reselling for over $6500, which is equal to a Return on Investment of 2500%.

Limited edition sneakers almost always sell for more than their initial retail value… if you can get your hands on them.

Downside: If you decide to wear the shoes you just bought, your first steps might cost you a couple of hundred dollars each.


This one goes over a lot of people’s heads, but wine is actually pretty well established as an investment. There are wine portfolios and wine portfolio managers, that pull returns of over 7% although they usually take hefty management fees and commissions. Wine can be one of the best performing investments, as long as you choose the right ones and refrain from drinking them yourself. The above-average return on investment for wine is often credited to China’s growing middle-class and demand for fine wine. Should you choose to invest in fine wine, be aware that there are also many fraudsters and scammers navigating the wine market, selling off-vintage wine and wine with falsified labels.

Investing in yourself

Cliché, I know. But instead of a made-up inspirational quote, here is one by Warren Buffet:

Investing in yourself means tackling areas you aren’t good at and learning new skills, address whatever you feel your weaknesses are, and do it now.

Whether you buy yourself a book, decide to get a higher education, or take a foreign language class, investing in yourself is one of the best investments you’ll ever make.

Someone’s crazy startup

Don’t get me wrong, this could also be the best way to lose money on this list, but imagine you had invested in your buddy Bill when he dropped out of college in 1975. That being said, keep in mind that for every Bill Gates out there, there is a million other college dropouts whose startups never took off.

Digital Securities

While regular Crypto Investments like Bitcoin and popular altcoins are long seen as established investments, blockchain technology enables an entirely new class of investment entities, the security tokens. While they’re technically just regulated, blockchain-based securities, what’s special about them is that they can represent partial ownership or profit participation of any asset you can think of, tangible or intangible. If you are interested in owning part of a windmill, a ship, or real estate, check them out!

Market volume of Security Tokens. Source: Finoa

Domain Names

Domain names can often sell for tenfold or more the initial investment value. The most sought-after domains are usually short, only contain one word or just a few letters and end

The domain sold for $345 million in 2007. Its buyer went bankrupt 2 years later.

There are few people who take domain hunting seriously and call themselves “Domainers.” Domainers try to either register or buy a domain they think is promising. The principle of domain hunting is quite easy: Buy or register the domain cheap when no one is using it and resell it to whoever wants it later. The biggest advantage they have over most other items on this list: You don’t need to physically store them. The biggest downside: You have to pay periodically to renew your ownership of the domain.

Collectors’ Items

That’s right, getting bullied in high school for collecting action figures might finally pay off. There are various collectors’ items that are worth a multitude of their retail prices today. The range of collectors’ items is vast: From Lego sets to Baseball Cards, these nostalgic items can provide enormous returns. The first Amazing Spider-Man comic cost 12 cents in 1963 and is now worth a whopping $40,000.

Disadvantage: Can’t take your action figures out of the box.

First page of a Gutenberg Bible, a book with an even higher ROI, but more of a multi-generation investment.


Your own health is the most important investment you can make. This doesn’t mean ONLY working out, it also means going to the doctor as needed. Avoiding medical care may result in late detection of disease, reduced survival, and potentially preventable human suffering and increased costs, studies suggest.


Investing in cars is a pricy and risky business. Just because a car is old, does not mean it’s rare, or worth anything. Great example: A Lamborghini Diablo from 1993 is worth about $260,000 today, while my 1993 Nissan Micra is worth about $300. When in doubt: Go for red and Italian.

Obvious upside: Showing off your vintage car, obvious downsides: Having to keep it in mind the car condition and the absence of airbags.

The Capital

How Being an Alcoholic Nerdy Sneakerhead With a Weakness For Baseball Might Make You Rich was originally published in The Capital on Medium, where people are continuing the conversation by highlighting and responding to this story.

Article Categories:
cars · finance · investing · sneakers · wine

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