You’d be hard-pressed to find a high-profile investor who’s more of a bitcoin bull than Michael Saylor. The cofounder of Strategy (Nasdaq: MSTR), formerly known as MicroStrategy, and bestselling author has repeatedly told people, “Never sell your Bitcoin (1).” Now, however, he seems to be retreating from his own advice.
After Strategy reported a $12.5 billion net loss in the first quarter of 2026 (2) — making it the third consecutive quarter of losses (largely because of the tumble in bitcoin prices earlier this year) — the company announced in early May that it would be offloading some of its crypto holdings.
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“We’ll probably sell some bitcoin to fund a dividend just to inoculate the market, just to send the message that we did it,” Saylor said in an earnings call with analysts (3). “The answer to how much we can sell responsibly is a function of where the bitcoin price is, and to a lesser extent, how the equity capital markets react.”
Strategy’s CEO Phong Le further distanced the company from Saylor’s credo on the call, saying “We will sell bitcoin when it’s advantageous to the company.”
“We’re not going to sit back and just say, ‘We’ll never sell the bitcoin.’ We want to be net aggregators of bitcoin, increasing our total bitcoin, but more importantly, increasing our bitcoin per share, because we think that is what is going to be most accretive long term for MSTR,” he added.
A wild ride
Cryptocurrencies have never been an investment vehicle for the weak-stomached, but bitcoin’s ride in recent months has been especially rollercoaster-like.
In early November 2025, it was trading for over $110,000 per token. By mid-February 2026, it had plunged to under $70,000. The ups and downs continued until April, when a quiet, sustained rise began to take hold. As of mid-May, bitcoin was trading around $80,000 (4).
Saylor, in announcing plans to sell, made it abundantly clear that his faith in the cryptocurrency hadn’t changed.
“Look, the company’s fine, the bitcoin’s fine, the industry’s fine. The world didn’t come to an end,” he said. “If you’re a short seller and your thesis is, ‘The company’s got to sell equity in order to fund the dividends,’ I would like nothing better than to rip your wings off.”
Read More: Almost 50 with no retirement savings? Here’s why you shouldn’t panic
A big reversal
Despite the aggressive stance, Strategy’s decision comes just three months after Saylor refuted the idea that Strategy would ever sell any of its holdings. Speaking to CNBC in February, he said, “If bitcoin falls 90% for the next four years, we’ll refinance the debt. We’ll just roll it forward … I expect we’ll be buying bitcoin every quarter forever (5).”
As of mid-May, Strategy holds 818,869 bitcoins that are worth around $65 billion, making it the largest corporate owner of the cryptocurrency (6). In his interview with CNBC, Saylor said that despite the fall in price, the company has two and a half years of cash reserves to make dividend and debt payments.
Betting on bitcoin
Even with the potential “red flags” that come with investing in crypto, about 41% of American investors consider it a good investment, according to Charles Schwab’s 2025 Modern Wealth Survey (7). And as for actual gains, a 2026 survey from Security.org found that 53% of crypto owners reported net gains over time, while just 21% said they experienced net losses (8).
For those who still have faith in crypto’s ability to rebound, platforms like Kraken make it easier than ever to invest. Buying and trading cryptocurrencies is straightforward with Kraken, whether you’re on a desktop or using the mobile app.
Using the platform, you can invest in 600+ cryptocurrencies, including Bitcoin, Ethereum, Solana, XRP and more, or you can set up recurring buys to invest automatically. There’s even the option to add price conditions so your trades only execute when the market hits your target.
Kraken also offers guides on popular coins, helping you understand what you’re buying and how to navigate the process from start to finish. And if you have questions, 24/7 support is available via live chat, phone or email.
For those who want greater control, Kraken PRO provides an even more advanced trading experience.
Designed for active traders, it features a highly customizable interface with real-time market data, advanced tools and detailed order types like stop-loss and take-profit to help manage trades more precisely. You can also trade across spot, margin and derivatives markets, monitor performance in one unified portfolio and tailor your dashboard with multiple data widgets to suit your strategy.
Opening an account is quick, with a simple sign-up and verification process, followed by setting up a short investor profile to get started.
*Not investment advice. Crypto trading involves risk of loss. View legal disclosures atkraken.com/legal/disclosures. The views and opinions expressed in this article are those of the author and do not necessarily represent the views or opinions of Kraken or its management.
Seeking expert counsel
For the investors who still aren’t sure what to make of the crypto rollercoaster, a financial advisor can offer a reality check, educating you about the potential risks and rewards of digital currencies and their impact on your overall portfolio.
But it’s important to find an advisor you trust — and one who understands the unique characteristics of crypto. But hiring an advisor can be a lifelong commitment, which might make or break your retirement.
That’s where Advisor.com can come in. The platform does the heavy lifting for you, vetting advisors based on track record, client ratios and regulatory background. Plus, their network comprises fiduciaries, who are legally required to act in your best interests.
Just enter a few details about your finances and goals, and Advisor.com’s AI-powered matching tool will connect you with a qualified expert best-suited for your needs and preferences.
The best part? Advisor.com lets you set up a free initial consultation, with no obligation to hire, to see if they’re the right fit for you.
Shifting to ETFs
In the end, if crypto still feels like too much of a gamble, exchange-traded funds (ETFs) may be a better match for your comfort level.
ETFs provide a regulated, liquid and diversified structure within a traditional brokerage account. They also offer instant diversification across major asset classes and sectors, so there’s no need to select individual stocks or bonds. Plus, ETFs can be tax-efficient, as they typically pass through fewer capital gains to investors.
Not only that, but ETF investing is incredibly accessible because of its low costs. That means anyone, regardless of wealth, can take advantage of it. Even small amounts can grow over time with tools like Acorns, an app that automatically invests your spare change.
Signing up for Acorns takes just minutes: All you have to do is link your cards, and Acorns will round up each purchase to the nearest dollar, investing the difference — your spare change — into a diversified portfolio of ETFs managed by experts at leading investment firms like Vanguard and BlackRock.
For instance, if you buy a donut for $3.25, Acorns will round up the purchase to $4 and invest the change in a smart investment portfolio. So a $3.25 purchase automatically becomes a 75-cent investment in your future.
With Acorns, you can invest in a dividend ETF with as little as $5. And, if you sign up today, Acorns will add a $20 bonus to help you begin your investment journey.
— With files from Chris Morris
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Article sources
We rely only on vetted sources and credible third-party reporting. For details, see oureditorial ethics and guidelines.
@saylor (1); Strategy (2); Yahoo Finance (3),(4); CNBC (5); BitcoinTreasuries.net(6); Charles Schwab (7); Security.org(8)
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.