Form DEFA14A Strategy Inc

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

(Rule 14a-101)

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SCHEDULE 14A INFORMATION

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Strategy Inc

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On September 25, 2026, Strategy Inc (the “Company”) launched a page on its website, strategy.com/mstr/vote (the "Page"), concerning the Company’s 2026 Special Meeting of Shareholders (the "Special Meeting") and business information about the Company. The Company made available on the Page an investor presentation (the "Investor Presentation"). The Page on which the Investor Presentation was posted, a copy of the slides presented, and a transcript of the presentation are set forth below as Annexes A, B and C, respectively. A banner concerning the Special Meeting was added at the top of each page of the Company’s website. The text of the banner is set forth below as Annex D. The Company also published the Investor Presentation on its YouTube channel (Strategy Inc), as set forth below as Annex E.

Additionally, on September 25, 2026, (i) the Company, (ii) Michael J. Saylor, the Company's Chairman of the Board of Directors and Executive Chairman, (iii) Phong Q. Le, the Company's President and Chief Executive Officer, and (iv) Chaitanya Jain, the Company's Director, Investor Relations, made posts regarding the Special Meeting on their respective X accounts. Copies of those posts are set forth below as Annex F.

Further, on September 25, 2026, Mr. Jain appeared on an episode of The Digital Credit Podcast (https://x.com/i/broadcasts/1wGWjlWEbzeKQ), which was broadcast live on X and hosted by Tim Kotzman, during which Mr. Jain discussed, among other things, the Special Meeting and certain of the proposals to be presented for shareholder consideration. A transcript of Mr. Jain’s remarks regarding the foregoing is set forth below as Annex G.

Annex A

Annex B

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Annex C

Transcript: Amendment to Pay Daily Dividends Presentation

Michael Saylor

Thank you for joining us today. I'm Michael Saylor, the Executive Chairman of Strategy. I'm here with Phong Le, our President and CEO and we're here to talk about an amendment to pay daily dividends.

This is the latest exciting development in the digital credit space. As you know, digital credit is a new asset class. It's scaled from nothing to 16 billion over 20 months. There have been a host of IPOs. We've done about five, but there are three other IPOs from other digital credit issuers and we think that this is just a revolution; a revolutionary, new innovation in the credit markets. And one of the great things about digital credit is just how quickly it's evolving.

We have five credit instruments. What we've seen is the most successful of our five digital credit instruments is Stretch (STRC) and we believe the reason it's successful is because it has the lowest volatility and the highest liquidity. And the way that you create low volatility and high liquidity is to shorten the duration of the instrument and to actively manage the credit, either actively managing the dividend rate, actively managing the capital markets activity around it, actively managing the reserves. And the higher the frequency of those adjustments, the lower the volatility of the instrument.

Why is digital credit growing so fast? It's because the effective yields are extraordinary. So, it's very high performance credit. Digital credit has more liquidity, higher effective yield, higher tax equivalent yield than any of the other credit instruments in the marketplace. And it's novel. It's new. So many people haven't heard about it. But if you're looking for performance, liquidity, then digital credit is offering that. That's why it's growing so rapidly.

Stretch itself is backed by US dollar assets; that gives us a 3.8 year USD duration. Its backed by BTC reserves. We've got $68 billion right now in BTC reserves; that's about 42 years of dividend duration. Stretch is six times over collateralized. That buyback program has been executed to about 1.1 billion in quantity. Stretch has currently got more than $100 million of daily liquidity and in excess of nine billion in notional outstanding. By any measure, it's one of the most successful preferred stocks ever and what we're doing here today is to make it better.

In addition to Stretch being a very powerful credit instrument, it's also emerging as a platform for digital money and digital yield. There's a really exciting, fast-growing ecosystem of partners, and there are a lot of different use cases. So let me share some of those.

What you'll see is there's a set of DeFi innovators that are creating stablecoin and stablecoin type instruments on top of STRC. There are a lot of digital assets innovators that are tokenizing STRC. We see STRC finding its way into funds, ETFs and ETPs, and people are building cash and yield accounts based on STRC.

The thing that we can do for them is to smooth out the cash flows, increase the liquidity, decrease the volatility. The stronger STRC is, then the better a platform it is for all of these other innovative products. And we think they're all nation right now, but they're destined to grow, and Stretch is destined to grow.

Our objective is for STRC to trade between $99 and $100, but generally we're targeting $100 par value. When it trades above $100, we have the ability to sell it into the market to strip the volatility above $100. If it falls below $100, we have the ability to buy it in order to damp the volatility. The closer we are able to get it to $100, the lower the vol. The lower the vol, the easier it is to get in and get out, the higher the frequency of the instrument.

And so, as you can imagine, we're thinking all the time about anything we can do in order to cause STRC to target $100 more effectively.

And to that end, we've gone through five different versions of STRC. The first version of STRC, when we launched the IPO in July of 2025, allowed for monthly dividend payments. That was an innovation. Variable rate dividend yields each month; that was the second innovation. And then we tied and tethered an at-the-market shelf registration to the instrument. That was the third innovation. By putting those three things together, we were able to create the most successful digital credit instrument in the market. In December, we upgraded it by adding in US dollar reserves to back STRC. Later that year, we put in place an initiative to provide semi-monthly dividends, so double the frequency of the cash flows. And then we followed that up by putting in place a stretch buyback program so that not only do we sell it above $100, but we can buy it back below $100. And that was a big innovation. A second innovation was to improve the governance and transparency around the US dollar reserve. So, we committed to the credit investors that US dollar reserves would only be used to pay dividends and interest and we put in place a one-year minimum; and so all of those things strengthened the backing of STRC.

And that takes us to now, version five, and the proposed next upgrade to digital credit is to convert our semi-monthly dividends to daily dividends, dramatically increasing the frequency of the cash flows and we hope dampening the volatility even further and therefore improving liquidity and improving this product so it reaches its full potential in the marketplace.

So, with that, I'm going to pass the floor to Phong, who's going to discuss the details, our thinking, and why we think this is in the best interest of all of our investors.

Phong Le

Thank you, Michael, and thank you for everyone for joining us today.

I'll start with thanking the investor base for approving semi-monthly dividends for Stretch in June of this year. And as a recap, 97.5% of the Stretch shareholders who cast a vote for this proposal supported the move to semi-monthly dividends and even more, 99.9% of our common shareholders voted in support of moving to semi-monthly dividends. We made that change to move from dividends paid once a month to twice a month on the 15th and month-end with the rest of the economics unchanged, and since then we've paid $255 million in Stretch semi-monthly dividends.

On the back of that success is our current proposal, which is to accrue and pay daily dividends for Strife, Stretch, Strike and Stride, all of our U.S.-based preferreds. And that would be a massive improvement; we would now accrue 15x more frequently dividends for Stretch and 90x more frequently dividends for our quarterly instruments – Strife, Strike and Stride. And even on top of that, we're moving to calendar day record dates and calendar day accruals for each of these instruments, with the next business day being the payment date. I'll walk through that a little bit more in detail later. And we will announce the Stretch rate (and the rate of all of these instruments), Stretch primarily, on the 15th day of the prior month. Our objective here - the design is to stabilize the price, dampen the cyclicality, drive liquidity, and grow greater demand in our preferred instruments.

So you'll see here a pictorial representation of the change of record dates. Currently, Stretch records 24 record dates per year, and we're moving to 365 record dates on most years and 366 on leap years. The improvement is even more pronounced for the current instruments that have quarterly record dates, four per year, moving at 365 per year.

How is the dividend calculated? The dividend will first be calculated by calculating the semi-monthly dividend as Stretch is calculated right now; which is taking the $100 stated amount, paramount, as an example, multiplying it by the 12%, in this case illustrative annual rate, which should then be $12, dividing that by 24, getting us to $0.50 paid on a semi-monthly basis. We'll then take that semi-monthly $0.50 and divide it by 15 calendar days for the 1st 15 days of the month, getting to a rounded $0.03 per day. And then for the next, anywhere between 13 and 16 calendar days, we'll divide that $0.50 by 13 up to 16 to represent the remaining daily dividends of the month.

If we take the month of November 2026 when we hope this to go live, this shows you all of the record dates and all of the payment dates. You'll see here every single Sunday through Saturday, every single holiday, including veteran's day and Thanksgiving in the US markets, will all be record dates and the payment dates will be on the business days, primarily Monday through Friday, excluding the holidays. And you'll see the actual payments here will be $0.03 on Sunday, $0.03 on Monday, $0.04 to account for rounding on Tuesday, and that occurs all the way through the 15th of the month where we'll pay the remaining amount that's due down at the 4th decimal.

The amendment timeline is as follows today. Our preliminary proxy is filed on September 25th. Voting will open shortly thereafter on October 5th when we file, or expect to file, our definitive proxy, and the voting will complete on October 28th at our proposed shareholder meeting date.

So how will the transition look? Stretch through the month of November, or, through the month of at the end of October/early November, will continue to pay as it is on a semi-monthly basis. And the 1st of November, November 1st, 2026, will be the first record date of the new cadence, and November 2nd, which is the first business day of November, will be the first payment date in the new cadence.

Strike, Strike, Stride, because they're paid on a quarterly basis, will complete the old cadence Q4 2026 with a final payment date December 31st, 2026. And starting the first day of January, January 1st, 2027, will move to the new cadence.

What are the benefits to the amendment that we're proposing? The first is this is a brand-new innovation and it will be the first global security in the world with calendar day accruals and dividends. We're pretty excited about that. Digital credit is meant to work every single day. Weekends and public holidays will count as record dates, and this better aligns the economics with the actual ownership periods, and also creates a better analogy or a mirror to the daily accrual that happens in money market funds today. It's also, in our opinion, built for the digital transformation of capital markets, which is rapidly accelerating, especially in the U.S., but around the globe. Bitcoin already trades 24/7. Equities are moving in that direction. So our preferred should also move in that direction. Tokenization is accelerating the shift towards global 24/7, 365 day a year markets. And so, the 365-day framework that we're proposing is designed for an always on financial system.

Why do we believe that this should or could reduce the volatility of our instruments? If you look here, this represents the change in Stretch behavior when we move from monthly to semi-monthly. When Stretch was monthly, we would see ex-dividend date, the day before the dividend date, about a 49-basis point decrease in price of the instrument. When we moved to semi-monthly, what we saw is on the ex-dividend dates about a 36-basis point drop in the price of the instrument. So that already was an improvement, and by moving to daily, we believe that this could also lead to lower volatility.

If this amendment is approved, there will be five preferreds in the world with a total market cap of $15 billion that pay daily dividends. There will only be four, the MSTR issue preferreds, that will pay daily dividends and also with 365-day daily accruals.

We think the amendment is quite favorable to preferred holders and let me recap why we think so. One is this is the next evolution and innovation of digital credit. We receive positive feedback from going monthly to semi-monthly. We see instruments paying daily on a business day basis, and we think moving to daily on a calendar day basis is the next logical evolution. That leads to a money market-like accrual cycle.

We think it will reduce the volatility, increase the liquidity, and strengthen the demand of all four of these preferreds. The lower month-end price volatility should also help those fund managers and their monthly marks. We also think this will become a more attractive instrument as an investment for interim cash. We've heard from institutional shareholders that there is undeployed interim cash that they can now put into an instrument like Stretch because they're receiving daily dividends. The faster dividend reinvestment should reduce the lag of dividend reinvestments, perhaps increasing the returns. And this will also potentially drive eligibility into low vol indices and unlock passive demand into our preferreds. And for those who are looking to lend with Stretch as collateral, this should also result in improved haircuts, advance rates, and collateral utility.

If you're a common shareholder, why do we think this amendment is favorable? One, by strengthening our preferred securities, they can create competitive advantages over other credit instruments, leading to greater inflows. Greater inflows into our preferred securities should improve our common shares - MSTR. That demand will drive Amplification and Bitcoin Per Share, which can increase the mNAV of our common and lower the cost of capital if we're issuing common, as an example, to pay these dividends. That'll drive more capital into Bitcoin with greater issuance of preferreds, and that should support the Bitcoin price growing strategy overall and completing the virtuous cycle that we have built with our Company.

Our ambition is to be the world's largest company in the world. And we already currently own the most Bitcoin in the world, 4% of total holdings. We think these amendments should help us issue the strongest digital credit in the world and improve Stretch, and that should also help us create the best equity in the world, MSTR, which will further help us increase our Bitcoin and our Bitcoin per share.

So, with that, I want to thank you all for listening to this proposal.

Annex D

Annex E

Annex F

Annex G

Chaitanya Jain (CJ)

So, you know, that's what digital credit is. And in terms of what we did today earlier this morning, it's a pretty monumental day for us - so, it's auspicious that we're speaking right now - as we announced that we're going to move our U.S.-listed preferred equity instruments, including STRC from either quarterly or semi-monthly dividend cadence, which is what they were at, to now a daily dividend cadence. Which means that if you hold these preferreds, you won't get paid just once every two weeks or once a quarter. You will get paid every single day. The way it works is every single calendar day is a record date. So, you accrue dividends every single day. It could be a weekend, a holiday, but you'll still be getting dividends on that day. The payment would happen on the next business day. And for us, this is a very unique and important feature of how we thought of the daily dividend upgrade, if you can call it that. Bitcoin already is 24/7. A lot of equities are going to go into the 24/7 model and, you know, trade every day. Nasdaq is announcing that they're going to move in that direction very soon. The tokenization trend is taking off, which means you can buy and sell equities every single day. So, we wanted to make sure that you also can earn the dividends on these preferred every day. So, we already think of all of these digital credit instruments as products in some sense - if you can call it that. They obviously are SEC-registered securities, but we sometimes think of it as products. And they are held by shareholders, but we sometimes think of them as customers. And you always think about what can we do to innovate and improve the product, improve the security to make it more attractive, more desirable for our customers or for our shareholders rather. And this was a very important step in that direction. So, we are very excited that we've sort of made this announcement today. We filed a preliminary proxy filing with the SEC. We'll file a definitive proxy filing in October, the first week, after which shareholder vote will open. So, all our MSTR common stock equity shareholders will get to vote on this amendment up until October 28th. So, it'll be open for about three weeks. And October 29th is our earnings call. So, around then is, you know, when we’ll likely have the result. So, we're very excited. And we're also very actively getting feedback from investors. So, if you have any feedback, we're always listening. So, always happy to hear feedback on this as well.

Tim Kotzman (Kotzman)

Yeah, I see the feedback coming in on social media in the comments. And it's always great to just have that immediate feedback. People that are excited about it, people that are surprised by it, people that want to vote. You know, maybe not yes for it. It's like very interesting to see all the feedback. The 365 record dates a year is super interesting. And it, I guess, hasn't been done yet. So, we don't maybe have an answer to this question. But how is Strategy thinking about the every day as a record date? Is there a world in which that improves liquidity and dampens volatility? Or is it more just for meme culture? Like I'm getting it's like Christmas day is a record date. I'm getting paid on Christmas day. Or as you alluded to, is it more so, at least initially, kind of aligning with that every single day, tokenization digital, everything going that direction in the US capital markets, and Strategy wanting to be aligned with that in real time?

CJ

So, I would say it's a combination of all of those reasons. And I should definitely start off by, you know, paying my respect to the team at Strive and what they've done with SATA. Matt Cole, Jeff Walton, Ben — they all are incredibly sharp people. And they've executed tremendously well with Strive. And obviously we observed how they took SATA from monthly dividends to daily dividends. And we studied their model very carefully and we realized that this is a good innovation. And then we were thinking about what's the right way for us to sort of move in this daily dividend direction as well. And the reasons are kind of as you laid out. The biggest one is the idea of why should dividends only accrue on business days? If you, in theory, when you compare it with other income instruments in the world or money market funds, for example, the dividends or the income accrues every single day with those kinds of funds or those kinds of instruments. So, we wanted to match that kind of a cycle a bit more and we wanted the economics to be aligned a lot closer to the actual ownership period that you have where you hold the stock or you hold the digital credit instruments. If you're holding STRC through a weekend, through holidays, then why shouldn't those dividends accrue then? We should just align the benefits exactly with the ownership period. And there is definitely some element of making this be perceived in a more desirable manner. There are — everyone wants to — sort of earn every day right. So, why shouldn't we lean into the angle of if — you know, Bitcoin trades 24/7 and if you in theory can work 24/7 and earn income for yourself, why can't your equity or your investments or your credit also pay you 24/7? So obviously we aren’t there yet where we can stream dividends every single hour or every single second. The world hasn't reached that point in terms of the technological integration between the DeFi and TradFi, and maybe someday we'll reach there who knows.

Kotzman

It seems like that's — it seems like that's coming, right?

CJ

Yeah, I mean, that would be really exciting and entertaining that might have a whole other set of issues to deal with, but for now I think it definitely makes sense that all the other preferreds in the world — almost all of them — pay quarterly dividends. And that was definitely very archaic. That's why we started ourselves with the first few preferreds. And then we realized STRC could be monthly. Then we did one upgrade — took it to semi-monthly. And now it naturally feels like the right thing to do and, you know, take it to daily. And that's also after seeing and listening to a lot of feedback that a lot of shareholders gave us. Definitely a lot of retail shareholders love the idea of getting paid daily. So we just thought that doing it 24/7 in some sense - or not 24/7 but seven days a week 365 days a year - is the right way to do it. So we're very excited, you know, with this upgrade.

Additional Information and Where You Can Find It

Strategy Inc (the “Company”) has filed a preliminary proxy statement with the Securities and Exchange Commission (the “SEC”) in connection with the 2026 Special Meeting of Stockholders (the “Special Meeting”). The Company also intends to file a definitive proxy statement with the SEC for the Special Meeting. Promptly after filing the definitive proxy statement, the Company will mail the definitive proxy statement and a proxy card to each stockholder entitled to vote at the Special Meeting. Investors and securityholders are urged to read these documents, including the definitive proxy statement (and any amendments or supplements thereto), when they become available because they contain important information. You may obtain these documents (when they become available) free of charge on the SEC's website (www.sec.gov) or at the Company’s website (www.strategy.com) or by contacting the Company’s Investor Relations team by email ([email protected]).

No proxy cards are being furnished by this communication. Stockholders may vote their shares only by following the voting instructions set forth in the definitive proxy statement.

Participant Information

The Company and its directors and executive officers may be deemed to be “participants” (as defined in Section 14(a) of the Securities Exchange Act of 1934, as amended) in the solicitation of proxies from Strategy’s stockholders in connection with the matters to be considered at the Special Meeting. Information about the compensation of our named executive officers and our non-employee directors is set forth in the sections titled “Executive Officer Compensation” and “Director Compensation”, respectively, in the definitive proxy statement for the Company’s 2026 Annual Meeting of Stockholders filed with the SEC on April 28, 2026, available here. Information regarding the participants’ holdings of the Company’s securities and their direct or indirect interests, by security holdings or otherwise, can be found in the sections titled “Security Ownership of Certain Beneficial Owners and Management” and “Interests of Directors and Officers” in the preliminary proxy statement for the Special Meeting, available here.

Forward-Looking Statements

Statements in this communication about future expectations, plans, and prospects, as well as any other statements regarding matters that are not historical facts, may constitute “forward-looking statements” within the meaning of The Private Securities Litigation Reform Act of 1995. These statements include, but are not limited to, statements regarding the proposed changes to the terms of the Company’s 10.00% Series A Perpetual Strife Preferred Stock, Variable Rate Series A Perpetual Stretch Preferred Stock, 8.00% Series A Perpetual Strike Preferred Stock, and 10.00% Series A Perpetual Stride Preferred Stock and related potential benefits or impacts. The words “anticipate,” “believe,” “continue,” “could,” “estimate,” “expect,” “intend,” “may,” “plan,” “potential,” “predict,” “project,” “should,” “target,” “will,” “would,” and similar expressions are intended to identify forward-looking statements, although not all forward-looking statements contain these identifying words. Actual results may differ materially from those indicated by such forward-looking statements as a result of various important factors, including the factors discussed under the caption “Risk Factors” in the Company’s Quarterly Report on Form 10-Q filed with the SEC on August 3, 2026 and the risks described in other filings that the Company may make with the SEC. Any forward-looking statements contained in this communication speak only as of the date hereof, and the Company specifically disclaims any obligation to update any forward-looking statement, whether as a result of new information, future events, or otherwise, except as required by law.