What’s Flying Higher Than Bitcoin? The Software Company Buying Up Bitcoin

Bitcoin prices have surged about 40% since Election Day. MicroStrategy has climbed even faster.

The software company turned itself into a bitcoin buying machine in 2020 and now holds some $37 billion worth of tokens. For many individual investors, the stock is a more popular bitcoin play than the cryptocurrency itself and they are willing to pay up for it.

With a $91 billion market value, MicroStrategy is trading at more than twice the value of its underlying bitcoin. The shares have soared more than sixfold this year and 77% since Nov. 5, with traders betting that the digital-assets industry will flourish under President-elect Donald Trump . Bitcoin prices are hovering just below $95,000, after trading near $100,000 last week.

“MicroStrategy found a way to outperform bitcoin,” Michael Saylor , the company’s founder and executive chairman, said in an interview. “The way that we outperform bitcoin, in essence, is we just lever up bitcoin.”

And Saylor says he is just getting started. He unveiled an audacious plan just days before the election to hire investment banks to raise $42 billion in capital over three years through stock and bond offerings to buy more tokens. His company had $4.3 billion in convertible debt outstanding as of Oct. 29.

MicroStrategy’s mix of bitcoin maximalism and Wall Street-style financial engineering has paid off for its investors, but skeptics question whether it is sustainable.

Saylor’s heavy use of leverage, or borrowed money, to buy bitcoin backfired during the 2022 crypto-market meltdown when the collapse of Sam Bankman-Fried ’s FTX dragged bitcoin prices below $16,000. Quarter after quarter, MicroStrategy incurred mounting losses tied to bitcoin and Saylor stepped down as CEO, a position he had held since 1989.

“This stock has become detached from reality,” said Andrew Left, a prominent short seller and founder of Citron Research.

Left describes himself as bullish on bitcoin itself and praised MicroStrategy in 2020 when it first began amassing bitcoin. But in a Thursday post on X , Left said he had taken out a bet against MicroStrategy, which caused its stock to tumble.

Some analysts warn MicroStrategy’s stunning run-up is part of a broader investor euphoria for speculative assets and will inevitably collapse. David Trainer, founder of research firm New Constructs, said MicroStrategy is a bad business by conventional metrics—for instance, it has posted a net loss for the past three quarters.

Michael Saylor’s heavy use of borrowed money to buy bitcoin backfired during the 2022 crypto-market meltdown. Photo: Alyssa Schukar for WSJ

“It’s symptomatic of a market that has become obsessed with believing in get-rich-quick schemes,” Trainer said. “If you like bitcoin, go buy bitcoin. But don’t invest in a company that’s losing money and also buying bitcoin, because then you’ve sort of doubled your risk.”

Some traders say a key part of the stock’s appeal is its volatility, which can help amplify their gains over a short period.

Garrett Shirey , a barber in Florence, Ala., bought one share of MicroStrategy at $436.53 in his retirement account Tuesday afternoon and sold it at $472.40 Wednesday morning, notching a quick profit.

Restricted from purchasing bitcoin in his Roth IRA account, the 39-year-old crypto enthusiast has had to settle for bitcoin proxies like MicroStrategy stock and bitcoin exchange-traded funds. He holds some shares of the Bitwise Bitcoin ETF .

“I don’t think bitcoin went up 8% in the last 24 hours, but MicroStrategy did,” said Shirey, who has been investing in cryptocurrencies since the pandemic.

Saylor said he came up with the bitcoin strategy in 2020 when Covid-19 forced lockdowns and the Federal Reserve cut interest rates to zero. MicroStrategy was competing with tech giants such as Microsoft and falling behind. The company was under pressure to return cash to shareholders through stock buybacks and dividends.

“It was either a fast death or a slow death, or take a risk, do something out of the box,” he said.

Saylor has often boasted about MicroStrategy’s volatility. “When you embrace volatility, then you’re outperforming the S&P,” he said during last month’s earnings call.

MicroStrategy’s volatility has helped it find ready buyers for its repeated issuances of convertible bonds—debt that can eventually be converted into shares, if the stock price rises to a specified level. Such bonds are often purchased by hedge funds that protect themselves against a collapse in the stock’s price by going short, or placing a bet that the stock will fall. Such funds generally don’t focus on whether the company is a good long-term investment, and instead seek to profit from the volatility of its stock.

MicroStrategy is an attractive trade for convertible-bond arbitragers, said Vadim Iosilevich, a veteran hedge-fund trader in New York.

“We can definitely agree that the volatility will be there,” he said.

Some investors are turning to ETFs that seek to amplify the return of MicroStrategy shares using borrowed money or derivative contracts. One such fund, the Defiance Daily Target 2x Long MSTR ETF aims to double the daily return of the stock and has attracted $1.8 billion in assets since it launched in August. Other funds allow traders to make inverse bets.

Chase Furey , a 25-year-old trader in Newport Beach, Calif., said he started buying bitcoin-related stocks including Coinbase Global, MicroStrategy and BlackRock’s bitcoin ETF in October. Hoping to turbocharge the gains, he moved all of his investments, worth about $112,000, into the Defiance ETF instead and has grown his portfolio to about $400,000.

The Harvard graduate, who studied economics in college, convinced his parents to let him manage $700,000 of their retirement assets. He said he came up with a “less dangerous and smarter” plan for them, investing 27% of their portfolio in the Defiance ETF and the rest in MicroStrategy shares. The money has more than doubled to $1.8 million, he said.

“I think bitcoin could hit $400,000 and I think MicroStrategy could possibly 10x from where it is now by the end of next year, so that’s kind of my game plan with that,” he said.

Even some bitcoin bulls have expressed unease about the risks investors face by betting on MicroStrategy. Mike Novogratz , the billionaire CEO of crypto-trading firm Galaxy Digital , warned in an interview on CNBC Thursday that bitcoin could fall 20% after peaking at $100,000—in part because of leveraged bets on MicroStrategy available through some exchange-traded funds.

“The crypto community is levered to the gills right now, so there will be a correction,” Novogratz said.

Superannuation is the first thought when it comes to self-funding retirement. Yet it is hardly the only option for doing so.

Just as we have a choice in how and where we work to earn a living, many people also have a choice in how to fund their retirement.

It is possible and sometimes preferable to leave your superannuation untouched, allowing it to continue growing. Some or all of your income can come from alternative sources instead.

Here are some alternatives you can consider.

1. Downsize your home

For many who own their own homes, the equity accrued over decades can eclipse the funds in superannuation. However, it’s theoretical money only until it is unlocked.

Selling up the family home and downsizing – or rightsizing – for retirement allows you to pocket those gains tax-free and simultaneously relocate to a more suitable home with lower upkeep costs.

Up to $300,000 from the proceeds can be contributed by a downsizer to boost your super, and the remainder can be used to fund living expenses or actively invested.

Remember that while the sale proceeds of your home are tax-free, any future profits or interest earned from that money will be taxable.

2. Part-time work

Semi-retirement allows you to gradually step into retirement. You continue earning income and super while working part-time, keeping a foot in the workforce while testing the waters of your new found free time.

Doing so also offers scope to move into different roles, such as passing on your skills to future generations by teaching/training others in your field of expertise, or taking employment in a new area that interests you and is closer to home.

3. Self-employment

Retirement from a full-time position presents a good opportunity to pursue self-employment. With more time and fewer commitments on your hands, you have greater scope to turn your hobby into a business or leverage your professional skills and reputation as an external consultant.

Also, for the self-employed and those with a family business, director’s loan repayments from the company are typically tax-free, offering a potentially lucrative source of

income and a means of extracting previous investments into the business without selling your ownership stake.

4. Investments

Rental property income (from residential or commercial properties) can supplement or even provide a generous source of income. The same applies to dividends from shares.

These are likely to be more profitable if you own them well before retirement.

Income that is surplus to your everyday needs can be reinvested using tax-effective strategies to grow your future returns.

5. Family trust

A family trust could be used to house investments for yourself and other relatives, building intergenerational wealth.

Trusts allow funds to be allocated to beneficiaries to manage marginal tax rates and stretch the money further, you have control over how income is split between different family members and have flexibility for changing circumstances.

6. Selling collectables

You may not realise the value of items you have collected over the years, such as wine, artwork, jewellery, vintage cars, and antiques.

Rather than have them collect dust or pay to store them, they could be sold to fund your living costs or new investments.

Where possible, avoid selling growth assets in a depressed market – wait until you can extract maximum value.

7. Obtaining a part-pension

Part-pensions are not only possible but valuable in making your superannuation stretch further. They still entitle you to a concession card with benefits in healthcare, transport, and more.

Take these savings even further by requesting pensioner discounts with other companies, on everything from utilities to travel and insurance to eating out.

Also, don’t overestimate the value of your assets as part of the means test. It’s a common mistake that can wrongly deny you a full or part-pension.

Plan ahead

However, you ultimately fund your retirement, planning is crucial. Advice would hopefully pay for itself.

Understand your spending and how those habits will change before and during retirement, then look to investments that offer the best fit.

Consider a mixture of strategies to diversify your risk, manage your tax liabilities and ensure ongoing income.

Above all, timing is key. The further ahead you plan, the more time you have to embrace additional opportunities and do things at the right time to maximise their value. You’ve worked hard and now is your chance to enjoy the fruits of your labour!

Helen Baker is a licensed Australian financial adviser and author of the new book, Money For Life: How to build financial security from firm foundations (Major Street Publishing $32.99). Find out more at www.onyourowntwofeet.com.au