How I’d Invest $250,000 In Today’s Bear Market


Let’s say you’ve currently got about $250,000 in cash. With the global financial recession building, opportunities are piling up. However, things could get worse in this bear market given we’re only nine months in. How would you invest it?

2022 has so far been a terrible year for both stocks and bonds. Real estate has outperformed stocks by over 25%. But even real estate is starting to fade as mortgage rates surge higher.

This post will go through how I plan to deploy $250,000 in today’s bear market. Maybe some of you have accumulated six figures in cash and are wondering what to do as well.

US treasury bond performance versus stocks
Nowhere to hide in 2022 except cash and real estate

How I’d Invest $250,000 Today

I’ve been accumulating a larger-than-normal cash hoard this year. Usually, I’ll have between $50,000 – $100,000 in my main bank account. But so far, I’ve accumulated over $250,000.

In addition to accumulating cash, I’ve also been dollar-cost averaging in the S&P 500 on the way down. I’ve also been dollar-cost average in private real estate on the way up. But these purchases are usually only in $1,000 – $10,000 increments.

Now that my cash balance is larger than normal, this is my thought exercise on how to deploy it.

Background Info Before Deploying The Cash

We consider ourselves moderately conservative investors since we don’t have regular day job income. We fear having to go back to work, not because we fear work but because we fear losing our freedom. As a result, we are unwilling to take too much investment risk. I’m 45 and my wife is 43.

Although we don’t have day jobs, we do generate enough passive investment income to cover our living expenses. We also generate online income, which is we mostly reinvest. Therefore, our cash pile will continue to build if we don’t spend or invest the money.

For life goals, we want to remain unemployed at least until our youngest is eligible for kindergarten full-time in 2025. Time feels like it’s accelerating with two young kids, so we want to spend more time with them now.

We’re also looking to upgrade our home in one to three years. That said, my wife and children would be happy living in our current home for the next ten years.

Our children’s educational expenses are covered after we superfunded two 529 plans. We also have life insurance and estate planning set up. Therefore, there’s no major big ticket items coming up.

Here’s how we’d invest $250,000 in today’s bear market.

1) Treasury Bonds (Targeting 60% Of The $250,000)

Only about 5% of our net worth is in bonds, individual muni bonds we plan to hold until maturity. Our target annual net worth growth rate is between 5% to 10% a year, depending on economic conditions. Therefore, being able to earn up to ~4.45% on a 3-year treasury bond is enticing.

At the same time, I’m always on the lookout for a nicer home because I believe living in a great house is the best way to enjoy our wealth. Think about all the time we spend at home nowadays.

There is no joy or utility derived from owning stocks, which is one of the reasons why I prefer investing in real estate over stocks. However, dividend stocks do provide 100% passive income.

Once the 10-year bond yield hit 4%, I decided to purchase the following Treasury bonds totaling $142,872.91.

  • $101,736.74,000 worth of 9-month treasury bills yielding 4.2%.
  • $10,766.89 worth of 1-year treasury bills yielding 4.3%
  • $15,501.33 worth of 3-year treasury bills yielding 4.45%
  • $14,867.95 worth of 2-year treasury bills yielding 4.38%
How I'd Invest $250,000 In Today's Bear Market - buying treasury bonds

Although locking in a 4.2% to 4.45% return won’t make us rich, it will provide us peace of mind. We also already feel rich, so making a more money won’t make us feel richer. Our focus is on optimizing our freedom and time.

Here’s a tutorial on how to buy Treasury bonds, which includes some buying strategies to consider.

2) Stocks (10% Of $250,000)

Roughly 24% of our net worth is in stocks. It was about 30% at the beginning of the year. Thanks bear market!

The range has hovered between 20% – 30% since I left work in 2012. Since I started working in equities in 1999, I’ve done my best to diversify away from stocks and into hard assets.

My career and pay were already leveraged to the stock market. And I saw so many great fortunes made and lost during my time in the industry. When I left work, I continued my preference of investing mostly in real estate.

Unfortunately, we front-loaded our stock purchases in 2022 through our kids’ Roth IRAs, custodial accounts, SEP IRAs, and 529 plans. For over 20 years, we’ve always front-loaded our tax-advantaged accounts at the beginning of the year to get them out of the way.

Most of the time it works out, some of the time it doesn’t. That’s market timing for you. But we do get to front-load our tax-advantaged investments again in 2023, which will prove to be better timing if the S&P 500 stays depressed.

In addition to maxing out our tax-advantaged accounts, we’ve been regular contributors to our taxable online brokerage accounts. After all, in order to retire early, you need a much larger taxable investment portfolio to live off its income.

I just don’t enjoy investing in stocks due to the day-to-day volatility and lack of utility stocks provide.

No Rush To Buy Stocks

If the Fed insists on raising the Fed Funds rate to 4.5%, then the S&P 500 could easily decline to 3,500. And if earnings start getting cut by 10%, then the S&P 500 could easily decline to 3,200 based on the median historical P/E multiple.

As a result, I’m only nibbling at these levels. The Fed says it plans to hike through the end of 2022 and reassess. With investors able to get a guaranteed 4%+ return in Treasuries, it’s hard to see the S&P 500 rebounding strongly until the Fed admits inflation has peaked.

Therefore, I’m just buying in $1,000 – $5,000 tranches after every 1% – 2% decline through the end of the year. If the S&P 500 goes below 3,500, I will increase my investment size.

3) Venture Capital / Venture Debt (20% Of The $250,000)

I enjoy investing in private funds because they are long-term investments with no day-to-day price updates. As a result, these investments cause little stress and are easy to forget about.

I’ve already made capital commitments to a couple venture capital funds from Kleiner Perkins. I also made a capital commitment to Structural Capital, a venture debt fund. As a result, I will just keep contributing to these funds whenever there are capital calls.

I expect venture debt to outperform venture capital (equity) during this time of higher rates. Venture debt is a lower risk way to generate returns in private companies.

3) Real Estate (10% Of The $250,000)

Real estate is my favorite asset class to build wealth. It provides shelter, generates income, and is less volatile. Unlike with some stocks, real estate values just don’t decline by massive amounts overnight due to some slight earnings miss.

No matter what happens to the value of our current forever home we bought in 2020, I’m thankful it has been able to keep my family safe and loved during the pandemic. When it comes to buying a primary residence, it’s lifestyle first, investment returns a distant second.

All the memories, photos, videos, and milestones our kids have achieved in our current house are priceless. Even when I was suffering from real estate FOMO earlier in the year, our kids said they prefer our much cheaper home. As a real estate obsessed father, that meant a lot.

Their response showed me the price of a home isn’t necessarily the main thing that makes it nicer. The house layout and its familiarity matters a lot too.

Given my wife and kids happy in our home, I shouldn’t try to buy another one so soon. Ideally, we live in our current home for at least five years (2025), save up a lot more money, and comfortably upgrade based on my net worth home buying rule.

Therefore, I will continue to dollar-cost average into private real estate funds like Fundrise, that invest in single-family homes in the Sunbelt. Prices and rents are cooling. However, Sunbelt real estate should be a long-term beneficiary of demographic trends, technology, and work from home.

I will be investing in $3,000 – $5,000 tranches through the end of the year.

Deployment Speed Depends On Your Certainty

When the investment return is certain, it’s easier to invest. When you’re certain you don’t need the money, it’s easier to invest for longer durations as well. But not all investments are created equal.

I deployed 60% of my $250,000 in Treasury bonds because I wanted to earn a higher return immediately. In fact, I’m actively trying to get my wife to invest in Treasury bonds and figure out a way to optimize our business cash as well. The investment is risk-free, so I have no fear.

I will most certainly fulfill my venture capital and venture debt capital calls when they come due. Otherwise, I will be banned from ever investing with these fund managers again. These investments have risks, but I want to diversify further.

I’m happy to keep investing in Sunbelt real estate funds, like I have since 2016, because I’m confident in the long-term demographic trend of relocating to lower-cost areas of the country. However, I’m also confident real estate prices and rents will fade over the next year, hence why I’m slowly legging in.

Finally, I’m certain I don’t like stock market volatility. I’m also uncertain how far central bankers will go to crush the middle class. As a result, I’m in no rush to buy and will focus on valuations.

It is discomforting to see your cash pile decline as you invest during a bear market. However, investing during a bear market tends to work out well over the long run. Further, if you maintain your income streams, your cash pile will replenish over time.

We know the average bear market lasts about a year. Hence, there’s a good chance we could get out of this rut by 2023. Taking advantage of higher guaranteed returns while legging into risk assets today sounds like the right thing to do.

Reader Questions And Action Items

Readers, how would you invest $250,000 today? Even if you don’t have $250,000, where would you invest your money? What type of investments do you think will generate over a 4.2% return over the next 12 months?

To gain an unfair competitive advantage in building wealth, read Buy This, Not That. It was written exactly for volatile times like these. I utilize my 27+ years of investing and finance experience to help you make better decisions.

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