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

Let’s say you’ve currently got a good amount of cash to invest. 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 20%. But even real estate is starting to fade as mortgage rates surged higher.

US treasury bond performance versus stocks - How to invest cash in this bear market
Nowhere to hide in 2022

How I’d Invest $250,000 Cash Today

After buying I Bonds, 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, partially due to a $122,000 private real estate investment windfall earlier this year.

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 averaging in Sunbelt real estate on the way up. But these purchases are usually only in $1,000 – $5,000 increments.

Now that my cash balance is larger than normal, this is my thought exercise on how to deploy it. If you have less than $250,000, that’s fine too. I share the percentages of where I will allocate my money.

Background Info To Understand Our Investment Process

I’m 45 and my wife is 42. Our kids our 5.5 and 3.

We consider ourselves moderately conservative investors since we haven’t had regular day job income since 2012 for me and 2015 for my wife. We fear having to go back to work, not because of work itself but because we fear losing our freedom with young children. As a result, we are unwilling to take too much investment risk.

Although we don’t have day jobs, we do generate enough passive investment income to cover our living expenses. This is our definition of financial independence.

We also generate online income, which we usually reinvest to generate more passive income. Therefore, our cash pile will continue to build if we don’t spend or invest the money.

For life goals, we both want to remain unemployed at least until our youngest is eligible for kindergarten full-time in 2025. This way, we can spend more time with both children.

After 2025, we might find day jobs or I might focus on becoming a professional writer. I enjoy being an author but it pays poorly.

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. Buying another home is not a priority.

Our children’s educational expenses are on track 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 cash in today’s bear market. This is what we’re doing with our own cash and not investment advice for you. Please always do your own due diligence before making any investment. Your investment decisions are yours alone.

1) Treasury Bonds (60% Of Cash Holding)

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. As a result, being able to earn up to ~4.8% on a 1-3-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 reached 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 cash 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 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. I will buy more Treasuries if the 10-year reaches 4% again, as you can purchase an unlimited amount, unlike I Bonds.

The one-year Treasury bonds yielding ~4.73% is especially attractive right now. The reason why is because it’s so much higher than the current 10-year Treasury bond yield at ~3.58%. As inflation and interest rates fade over the next 12 months, one-year Treasury bonds and longer durations will look more and more attractive.

Bond chart by year duration and yield

The remaining 39.9% of our cash will be invested in risk assets.

2) Stocks (10% Of Cash Holdings)

Roughly 27% 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 23 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.

No Rush To Buy Stocks

If the Fed insists on raising the Fed Funds rate to 5% and ruin the world, then the S&P 500 could easily decline below 3,600. And if earnings start getting cut by 10%, then the S&P 500 could 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. Although, the decline in the Series I Bond rate makes me more bullish.

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.

Given the situation, 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 3,600, I will increase my investment size to $3,000 – $5,000 a trade.

If I was in my 20s and 30s, I would allocate 60% of my cash to buying stocks instead. 30% would go to online real estate and the rest to Treasuries and education.

3) Venture Capital / Venture Debt (20% Of Cash Holding)

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.

The biggest downside to investing in these funds is higher fees. We’re talking 1-3% of assets and 20-30% of profits.

4) Real Estate (10% Of Cash Holding)

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 small earnings miss. Real estate accounts for about 50% of our net worth.

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 are 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 $1,000 – $3,000 tranches through the end of the year.

5) Debt Pay Down (0% Of Cash Holding)

In a high inflation and rising interest rate environment, I’m not paying down any extra mortgage debt. I already paid down some mortgage debt at the beginning of the year when inflation was high and Treasury bond yields were low.

At the time, it was a suboptimal move since it’s best to keep your negative real interest rate mortgage for as long as possible. High inflation was paying off the mortgage debt for me. But I paid off some mortgage debt anyway because it felt good and I was uncertain about stocks.

In retrospect, paying down some mortgage debt in 2021 was the right move as it saved me from losing ~20% had I invested the cash in the stock market. Hence, if you have debt, consider following my FS DAIR investing and debt pay down framework. This way, you’re always making financial progress.

Today, with inflation still high but Treasury bond yields much higher than mortgage rates, it makes no sense to pay down a negative interest mortgage rate. Instead, it’s better to buy Treasury bonds and live for free, which I’m doing.

If you have revolving credit card debt or auto loan debt, I’d follow my FS DAIR framework and accelerate paying down principal. You want to benefit from rising interest rates not get hurt by it.

Just make sure you don’t compromise your liquidity too much in a bear market. Always have at least six months of living expenses in cash.

6) Education (0.1% of Cash Holding)

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For example, for only $20 after tax you can order my bestseller, Buy This, Not That and immediately gain a competitive advantage to building wealth. You’ll also learn how to make more optimal decisions on some of life’s biggest dilemmas.

You could also subscribe to my free weekly newsletter and my free blog posts to stay on top of timely financial topics. The more you immerse yourself in money topics, the more you will learn and take appropriate action to help boost your wealth.

You can also go to YouTube, Khan Academy, or MOOC and watch hundreds of hours of free educational videos. Or you can pay for online courses to get even deeper into a subject.

Ignorance is no longer an excuse given how accessible education is today. Please allocate some of your budget to continuing education. Over time, the combination of experience and education will dramatically improve your confidence, wealth, and peace of mind.

Deployment Speed During Depends On Your Certainty

When the investment return is certain, it’s easier to invest cash. 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 have 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 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 rich central bankers will go to crush the middle class. As a result, I’m just nibbling and will focus on valuations.

It is discomforting to see your cash pile dwindle 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 every month.

We know the average bear market lasts about 15 months. Hence, there’s a decent chance we could get out of this rut some time in 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 To Invest Cash

Readers, how would you invest $250,000 cash in today’s bear market? 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. Click the image to pick up a copy today.

For more nuanced personal finance content, join 55,000+ others and sign up for the free Financial Samurai newsletter. I recap the week’s main events and share my candid thoughts. 

How I’d Invest $250,000 Cash In Today’s Bear Market is written by Financial Samurai for

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WATCH: Rapper Tells Joe Biden Voters ‘Get Out of My Concert’

WATCH: Rapper Tells Joe Biden Voters 'Get Out of My Concert'

( – Rapper Waka Flocka urged “all Joe Biden voters” to “get out of my concert” during his Monday performance in Salt Lake City, Utah.

(Viewer Discretion Advised)

Concertgoers could be seen applauding the rapper’s proclamation by raising their arms and making the amiable “hang loose” hand sign.

Following his statement, Waka Flocka began to sing “Grove St. Party,” a song from 2010.

Viewers used social media to voice various opinions; some expressed disapproval of the artist, while others offered support.

“As much as I don’t like Joe Biden this was wrong,” one X user reacted. “They paid money for a show like everyone else and while performing a show they should keep politics out of it.”

“This is wrong to be honest everyone is entitled to vote who they want,” another echoed.

Another wrote, “Insane,” while another stated, “This isn’t right.”

Not everyone in the comment section felt the same way.

“We need more of this,” one X user wrote.

“This is great and is a liberal’s nightmare!” another exclaimed.

“I normally would be against this type of political bullying, but seeing how everyone on the left treated those who wore MAGA hats in 2017, this is a dose of what goes around comes around,” a third said.

“Give them a taste of their own medicine,” another echoed.

“Waka funny af doing this omg lol,” another X user laughed.

“Good. This needs to happen more,” another declared.

It’s no secret that Waka Flocka supports President Trump. In October, the rapper endorsed the 45th president’s 2024 bid for the White House by posting a photo of himself alongside Trump.

More rappers appear to be open about supporting President Trump ahead of the 2024 presidential election.

It’s not looking too good for Joe Biden or the Democratic Party.

Copyright 2024.


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IRS Out For Blood More Than Doubling Penalty Interest

IRS taxes increase

In a blatant act of financial tyranny, the IRS is intensifying its assault on hardworking Americans by shamelessly jacking up the interest penalty on underpaid taxes from a pitiful 3% to an exorbitant 8%. This calculated move, recalibrated quarterly, serves as a stark reminder of the insatiable appetite of the IRS, an oppressive behemoth relentlessly extracting every last penny from citizens already shackled by burdensome taxation.

Specifically targeting non-corporate taxpayers, the IRS demands the federal short-term rate plus an additional three percentage points, a blatant money grab that directly targets struggling self-employed individuals, independent contractors, and gig economy workers. These individuals, already grappling to make ends meet, find themselves in the crosshairs of a government voraciously hungry for more of their hard-earned wages.

For those daring to resist this blatant financial coercion and falling short on their payments, brace for the punitive underpayment penalty. There’s a meager concession – if the amount due is under $1,000 after begrudgingly considering credits and other tax factors, citizens might receive a temporary reprieve from the claws of the taxman.

This audacious maneuver puts the self-employed and independent contractors in the IRS’s oppressive grip, coercing them to make quarterly estimated tax payments under the looming threat of severe financial retribution. The January 16, 2024 deadline for the fourth quarter of 2023 is fast approaching – a date that casts a dark shadow over those grappling with the suffocating weight of government overreach.

While the regular W-2 employees might momentarily sigh with relief as taxes are conveniently siphoned from each paycheck, tax experts issue a stern warning against such complacency. Joseph Doerrer, a CPA and financial planner from New Jersey, challenges individuals to scrutinize their tax situation, posing the provocative question, “Are you where you should be?” A question that echoes as a stark reminder of the government’s overreach into the pockets of hardworking Americans.

One taxpayer, Sameet Durg, found himself blindsided by an underpayment penalty reaching into the thousands – an unwelcome surprise that serves as a chilling testament to the relentless demands of the IRS. Durg, a marketing executive, now watches his finances with unwavering vigilance, refusing to endure a hefty hit come April.

As the IRS unabashedly cranks up the interest penalty, taxpayers are left grappling with the heavy-handed tactics of an agency that seems insatiable in its quest to confiscate more of their hard-earned money. This move underscores the urgent need for citizens to vehemently resist the oppressive tax regime, actively defy the IRS’s overreach, and reclaim sovereignty over their wages.

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GUILTY! Sam Bankman-Fried Faces Over 100 Years in Prison

GUILTY! Sam Bankman-Fried Faces Over 100 Years in Prison

( – Sam Bankman-Fried has been found guilty of all charges related to the collapse of his Bitcoin exchange, FTX.

“A New York jury in Manhattan federal court agreed with prosecutors that Bankman-Fried defrauded investors, customers and lenders in connection with the collapse of his crypto empire,” reported Fox Business.

“Prosecutors accused Bankman-Fried, who founded and controlled both FTX and sister hedge fund Alameda research, of misappropriating and embezzling billions of dollars in FTX customer deposits, scheming to mislead investors, and instructing other executives at his businesses to do the same,” it added.

Bankman-Fried was charged with five charges of conspiracy and two counts of wire fraud in the first two criminal trials.

The maximum sentence for each crime was 110 years in prison.

The hearing for Bankman-Fried’s sentence has been scheduled for March 28.

The Southern District of New York’s U.S. attorney, Damian Williams, commended the decision and said that Bankman-Fried “perpetrated one of the biggest financial frauds in American history.”

“The cryptocurrency industry might be new, the players like Bankman-Fried might be new,” Williams said. “But this kind of fraud, this kind of corruption, is as old as time.”

NBC News gave some background information and historical context before the decision:

“FTX and Alameda quickly collapsed in November 2022 after some of their financial liabilities were exposed.

The fact that Alameda had taken billions of dollars from FTX’s customers and that much of Alameda’s balance sheet was comprised of digital currency assets it had created was central to the case against Bankman-Fried.

Unnerved by disclosures about the firm’s financial position, many of FTX’s customers tried to get their money back. That set off the equivalent of a bank run.

The value of Alameda’s investments crashed, and FTX couldn’t return much of that money because it had been given to Alameda. Some went to the fund’s lenders, and billions were spent on sponsorships, commercials, and loans to top executives. That, too, was a major part of the case against Bankman-Fried.”

Following the collapse, more FTX and Alameda executives were prosecuted, including former CEO of Alameda Caroline Ellison, co-founder of FTX Gary Wang, and chief technology officer of FTX Nishad Singh.

All three pleaded guilty, agreed to cooperate, and testified against Bankman-Fried.

In exchange for their cooperation, they will receive less severe punishments.

In his defense, Bankman-Fried stated that he never intended to deceive anyone and that, following the failure of FTX and Alameda, the government had been searching for someone to blame.

“Mr. Bankman Fried maintains his innocence and will continue to vigorously fight the charges against him,” Mark S. Cohen, counsel to Bankman-Fried, said in response to the verdict.

Williams stated that he hoped the conviction would be an example for others.

“It’s a warning, this case, to every single fraudster out there who thinks that they’re untouchable, or that their crimes are too complex for us to catch, or that they’re too powerful for us to prosecute, or that they could try to talk their way out of it when they get caught,” Williams said. “Those folks should think again.”

Copyright 2023.

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