7 Unconventional Ways Regular People Can Invest Like the Super Rich

Matt Stefan
8 min readJun 1, 2022

There are more ways than ever to invest your money.

Changing government regulations, the digitization of money, and fractional ownership has created a plethora of investing options for regular people. For the first time in history, regular people can invest like the super rich.

These 7 unconventional investments might not make you super rich over night, but they may help you sleep better at night knowing all your money isn’t tied up in the stock market.

As the son of an investment advisor who has spent the last ten years working in tech, I am keenly interested in where technology and investing intersect. Over the last five years, I’ve been experimenting with unconventional investment strategies.

So far, I’ve built a modest crypto portfolio, started angel investing, and just purchased my first shares in a rare work of art. My timeline on these investments is relatively short but so far I’m not broke… or rich either.

However, I’ve learned a lot, met tons of interesting people, and had lots of fun along the way.

1. Rare Art

Art has proven to be one of the best investments of all time.

In fact, while the S&P declined 5.1% in 2018, the art market returned 10.6% and was called “the best investment of 2018” by The Wall Street Journal. It’s hard to argue with results like that.

Where to start:

Masterworks: founded in 2017, they are the first company to allow investors to buy shares of masterpieces by artists like Picasso, Monet, and Warhol.

  • Minimum investment = $10,000*
  • Risk Level = Medium
  • Liquidity = Low

How it works:

  1. Masterworks buys a painting.
  2. Take it public as an investable security.
  3. Sell shares in the artwork to investors.
  4. At some point later in the future, they sell the painting and distribute the profits

Note:

  • Masterworks is motivated to let purchasers in so you can reduce the minimum investment by emailing their support team

2. Real Estate

90% of millionaires invest in real estate.

Commercial Real Estate is a large legacy asset class that’s built generational wealth for many families. The only problem is that it requires lots of money, time & expertise, making it inaccessible to everyone but the top 1%.

Enter — the concept of PropSharing. New platforms allow you to purchase pieces of real estate and build a custom portfolio of properties to buy and sell as you please.

Where to start:

Willow: Willow is Canada’s first PropSharing investment platform, making it possible for people to buy fractions of properties.

  • Minimum Investment = Determined by Willow after application
  • Risk Level = Low
  • Liquidity = Low

How it works:

  1. They buy a building.
  2. Incorporate it as a special purpose vehicle (SPV).
  3. Investors become limited partners (LPs) in the property.
  4. Receive passive income, reports, and payouts when the building sells.

3. Private Markets (Startup Companies)

Since 2000, private market assets have grown 10x, representing over $6 trillion globally.

Many net-worth individuals maintain a large portion of their portfolio in private markets. That said, it takes lots of money, insight and luck to become a successful private market investor. The risk is high but the rewards can be life-changing. People who invest in the private market are often called angel investors. They invest their own money into early stage companies, typically in exchange for equity in the company.

Thanks to changes in government regulations, angel investor groups, and new digital marketplaces, it is easier than ever to get started in angel investing.

Where to start:

FrontFundr: provides access to Canada’s private markets by enabling all Canadians to invest in companies they would like to see succeed or believe will generate a return.

  • Minimum Investment = $100
  • Risk Level = High
  • Liquidity = Low

Republic: provides access to access highly-vetted investment opportunities in startups, real estate, video games, and crypto internationally. The republic ecosystem has deployed over $800 million in investments, has supported over 600 companies, and boasts a community of over 1.5M users across 100 countries.

  • Minimum Investment = $10
  • Risk Level = Medium
  • Liquidity = Low

Startup TNT (AB, SK, MB): Startup TNT runs semi-annual investment summits that provide an approachable way to become an angel investor. By pooling resources, knowledge, and capital, investors ‘syndicate’ together and make bets on companies as a group.

  • Minimum Investment = $5,000
  • Risk Level = Medium
  • Liquidity = Low

Valhalla (BC, AB, SK, MB): One of Canada’s most active angel investment groups that has collectively invested more than $71m since 2003. Investors become members to gain access to investment opportunities sourced by Valhalla.

  • Minimum Investment = $5,000
  • Risk Level = Medium
  • Liquidity = Low

How it works:

  1. You or an angel group finds companies looking to raise money
  2. You determine the terms for the investment
  3. You sign a ‘Term Sheet’ and invest your money
  4. You are issued shares in the private company or angel syndicates special purpose vehicle (SPV)

Note:

  • In Canada, you must be an accredited investor to become and Angel Investor, with a few exceptions
  • There are tax credits available to angel investors (some up to 45%), depending on what province you’re located in

4. Trading Cards

If you invested in both stock and trading cards a decade ago, your card portfolio would be worth nearly twice as much.

During the pandemic, the value of trading cards spiked. Notable investors like Gary Vaynerchuk and Logan Paul have been touting the investment opportunity surrounding trading cards for the last couple years.

For investors, trading cards are where passion meets profit. The asset class is relatively inflation proof and has a long history of stable returns. It’s also more fun than the stock market.

Where to start:

Unfortunately in Canada, there are no platforms that currently offer fractional ownership in trading cards. The best way to get started is to do your own research and buy cards through traditional dealers or website like ebay.

Collectable (US Only): offering some of the most iconic and rare sports collectibles in the world, curated by experts for their historical and cultural significance and prospective performance over time.

  • Minimum Investment = $100
  • Liquidity = Medium
  • Risk = Low

5. Cryptocurrencies

The total value of all digital currencies has swelled to about $2 trillion.

Due to their digital nature and often limited supply, cryptocurrencies offer an interesting alternative store of value to stocks or traditional money. They’re extremely volatile which creates the opportunity for outsized returns. Not for the faint of heart, cryptocurrencies offer the highest liquidity and highest risk of any asset on this list. Save maybe number 7.

Where to start:

Coinbase: the easiest place to buy and sell cryptocurrency.

  • Minimum Investment = $10
  • Risk Level = High
  • Liquidity = High

WealthSimple: Canada’s first regulated crypto platform.

  • Minimum Investment = $10
  • Risk Level = High
  • Liquidity = High

Newton: Canada’s trusted low-cost crypto trading platform.

  • Minimum Investment = $10
  • Risk Level = High
  • Liquidity = High

How it works:

  1. Create an account with one of the exchanges listed above
  2. Add money to your account via E-transfer or Visa
  3. Purchase your desired cryptocurrencies

Note:

  • Some card issuers will block transactions to crypto exchanges or charge extra fees
  • Exchanges require your contact information for any transaction over $1,000

6. Non-Fungible Tokens (NFTs)

In December 2021, an NFT sold for $91.8 million.

NFTs are digital collectibles that have software code embedded within them. That code can be used to trace back to the owner and establish authenticity. Much like other collectibles, owning NFTs confers status — like hanging a Picasso in your living world.

The total value of NFTs traded every week continues to hover around $2BN. Although the market is still in its infancy, this is an unconventional investment strategy that investors should keep on their radar.

Where to start:

LooksRare: community-first NFT marketplace where you can earn rewards for buying and selling on the platform.

  • Minimum Investment = $10
  • Risk Level = High
  • Liquidity = High

OpenSea: the world’s first and largest NFT marketplace.

  • Minimum Investment = $10
  • Risk Level = High
  • Liquidity = High

How it works:

  1. Setup a crypto wallet.
  2. Buy some crypto.
  3. Purchase an NFT.

7. Put It On Black

You have a 47% chance of doubling your money if you put it on black at the roulette table.

Where to start:

A casino near you!

  • Minimum Investment = $1
  • Risk Level = High
  • Liquidity = High

Conclusion

There are more ways than ever before to invest your money.

Changing government regulations and new technology is making it possible for regular people to invest like the super rich. Depending on your risk appetite and liquidity preference, alternative assets are a good way to diversify your portfolio.

Now is a good time to consider experimenting with unconventional investment strategies. Uncertain times call for unconventional methods. I believe the best way to learn is to dive in with an amount of money you can afford to lose. From there just relax, have fun, and manage your expectations!

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Matt Stefan

Creator of Chat Capital, the most approachable way to explore trends in finance and tech.