Go inside Strategy's Bitcoin playbook with CJ. Discover how they're using financial jiu jitsu to stack more sats and leave fiat plebs in the dust.
Timestamp Overview
[00:00:02 - 00:02:24] CJ’s Role on Saylor’s Elite Squad
- Chaitanya Jain (CJ) explains he’s part of MicroStrategy’s Bitcoin treasury team, basically the guys who execute Saylor’s gigabrain plays.
- His team handles raising capital, talking to investors who are finally waking up, and most importantly, buying and holding the damn Bitcoin.
- They also help Saylor with his Bitcoin advocacy, spreading the gospel of sound money to the uninitiated.
- The team is growing, adding more firepower to accelerate the mission. They’re not just buying Bitcoin; they’re building a financial fortress.
[00:02:24 - 00:06:29] The Only Metric That Matters: Bitcoin Yield
- Joe asks about the most important metric for a Bitcoin treasury company.
- CJ explains that for long-term hodlers, the key is the anticipated “BTC yield” over a decade.
- This basically means, “how much more Bitcoin will I own per share in the future?” It’s about accumulating more of the asset, not just watching the fiat price.
- He dismisses short-term price performance as noise. As long as the company is increasing its Bitcoin per share, it’s winning.
[00:06:29 - 00:09:24] Why MSTR Isn’t a Degenerate Leveraged ETF
- Joe asks why MSTR’s stock doesn’t perfectly mirror Bitcoin’s price every single day.
- CJ clarifies that MSTR is not built to be a 2x daily leveraged gambling tool. It’s engineered for long-term outperformance over 5-10 years.
- Daily price moves are just market noise from paper-handed sellers.
- The real value comes from constantly increasing the Bitcoin per share, which builds a rising floor under the stock price over the long run.
[00:09:24 - 00:11:42] The Right Time Horizon is Forever
- CJ echoes Saylor’s famous quote: the short term is 4 years, the medium term is 10 years, and the right term is forever.
- MicroStrategy makes decisions based on a 10, 20, or 30-year outlook, aiming to maximize value for shareholders over generations.
- While the company is focused on the long term, they’ve also created an entire ecosystem for traders who want to play with options and leverage, feeding off the volatility.
[00:11:42 - 00:15:37] Using Volatility to Get Cheap Capital
- CJ explains how MSTR weaponizes volatility. By issuing convertible debt, they essentially sell the stock’s future price swings to get incredibly cheap loans.
- He advises smaller companies to get smart leverage on their balance sheets.
- The key is to avoid stupid leverage: don’t use your Bitcoin as collateral and don’t take on short-term debt that could get you rekt in a downturn. Think in 4-year cycles, minimum.
[00:15:37 - 00:19:03] The Evolution: From Converts to Perpetual Preferreds
- Joe asks why MSTR shifted from convertible debt to preferred equity.
- CJ explains it was a massive upgrade. Convertible debt was only for big institutions, making it illiquid and mispriced.
- Preferred equity is a superior instrument. It can be perpetual (like a loan that never has to be repaid), it’s traded on NASDAQ so any pleb can buy it, and it solves all the problems of the old model.
[00:19:03 - 00:22:45] Saylor, AI, and the Bitcoin Treasury Playbook
- Joe asks who the mad genius is behind these financial products.
- CJ confirms it’s largely Michael Saylor, supercharged by AI tools like ChatGPT. Saylor is a power user, constantly researching and generating ideas.
- He says other Bitcoin treasury companies shouldn’t try to be clever; they should just copy-paste MicroStrategy’s playbook. It’s open-source financial domination.
[00:22:45 - 00:26:58] The Virtuous Cycle of Leverage and Premium
- CJ explains how smart leverage justifies MSTR trading at a premium to the value of its Bitcoin holdings (the MNAV).
- Leverage guarantees that the Bitcoin per share will grow over time. This future growth is priced in today, creating the premium.
- This premium then allows them to sell more stock to buy even more Bitcoin, accelerating the cycle. It’s a feedback loop of pure genius.
[00:26:58 - 00:33:22] STRC: The “iPhone Moment” for Bitcoin-Backed Yield
- MSTR’s preferreds are for everyone, from hedge funds to retail investors.
- CJ highlights STRC (“Stretch”) as a game-changer. It’s a high-yield product designed for price stability, stripping out Bitcoin’s volatility.
- He calls it the “iPhone moment,” a simple product that finally made his mom understand the value of Bitcoin. It’s designed for retirees and anyone who wants a high yield backed by the hardest money on earth.
[00:33:22 - 00:37:38] A Superior Alternative to Worthless Stablecoins
- CJ explains that STRC is designed to trade near its $100 face value, with a dividend that adjusts to keep the price stable.
- He notes that recent laws prohibit stablecoins from offering yield, positioning STRC as a unique, SEC-registered security that can offer yield.
- It’s a direct competitor to the $250 billion stablecoin market, offering a superior, yield-bearing alternative powered by Bitcoin.
[00:37:38 - 00:40:41] It’s Not a Speculative Attack, It’s a Peaceful Evolution
- Joe brings up the idea of a “speculative attack” on fiat currency.
- CJ reframes it. It’s not an “attack,” which sounds aggressive and alienates people.
- He calls it an “evolution,” not a revolution. They are simply swapping a weak, depreciating currency (USD) for a strong, appreciating asset (BTC) to create value. It’s about building a better financial system.
[00:40:41 - 00:43:55] Harvard’s Endowment Finally Bends the Knee
- CJ discusses Harvard’s endowment finally buying $100 million of a Bitcoin ETF.
- He’s happy but not surprised, seeing it as a sign of the inevitable institutional adoption. The old guard is finally waking up.
- He jokes that even after gifting Bitcoin books to all his Harvard professors, none of them reached out. The endowment managers figured it out on their own because they had a “need to know” to survive.
[00:43:55 - 00:52:15] MSTR Puts Short Sellers on Notice
- CJ touches on Bitcoin’s long-term growth rate, which is expected to crush the S&P 500.
- He then explains MSTR’s new transparent guidance on when they will sell stock. They won’t dump shares on the market unless the stock is trading at a high premium (above 2.5x MNAV).
- This move provides clarity to investors and is a direct shot at short sellers, removing the uncertainty they thrive on.
[00:52:15 - 00:59:21] Wall Street’s Incentives Have Flipped
- CJ explains how MSTR is revolutionizing investor relations with video earnings calls and real-time data.
- He makes a critical point: Bitcoin is now the biggest fee generator for Wall Street. Banks are making fortunes from MSTR’s IPOs and other Bitcoin products.
- The banks will always follow the money. Their financial incentives are now aligned with Bitcoin’s success, turning former enemies into powerful allies. The war for capital is being won.
Notable Quotes
The Forever Time Horizon
The short term horizon is four years, the medium term horizon is 10 years. And the right term horizon is forever.
Chaitanya Jain @_ChaitanyaJ
Leverage Strategy
You don't want to necessarily be posting your Bitcoin as collateral. You don't necessarily want to take short-term leverage.
Chaitanya Jain @_ChaitanyaJ
Saylor's Genius
It's a lot of him and ChatGPT back and forth and a lot of inputs and coordination with the team.
Chaitanya Jain @_ChaitanyaJ
Copy the Playbook
A simple copy paste might not be a bad idea for most Bitcoin treasury companies.
Chaitanya Jain @_ChaitanyaJ
The Virtuous Cycle
The credit is necessary to get the equity issuance.
Chaitanya Jain @_ChaitanyaJ
STRC: The iPhone Moment
I really think stretch is that iPhone moment for us. It's going to unlock a lot more capital.
Chaitanya Jain @_ChaitanyaJ
Understanding Bitcoin
After thousands of hours of explanation, she said, 'You know, now is when I finally sort of understand Bitcoin and see the value of Bitcoin.' And first, I was like, what? No, that makes no sense.
Chaitanya Jain @_ChaitanyaJ
The Monetary Evolution
It's not a revolution. It's an evolution.
Chaitanya Jain @_ChaitanyaJ
Harvard Wakes Up
The endowment kind of just works on its own separately. And they have a need to know.
Chaitanya Jain @_ChaitanyaJ
Bitcoin vs. S&P 500
It should because of these reasons have a perpetual growth rate greater than the S&P 500.
Chaitanya Jain @_ChaitanyaJ
Wall Street's New Incentive
Banks will always follow the money and the money right now is selling Bitcoin backed securities.
Chaitanya Jain @_ChaitanyaJ
Questions & Answers
Question 1: What is the most important metric for evaluating a Bitcoin treasury company?
Answer: Chaitanya Jain states that for a long-term investor, the single most important Key Performance Indicator (KPI) is the anticipated Bitcoin Yield (BTC Yield) over a 10-year horizon. This metric focuses on the growth of Bitcoin per share, reflecting the company’s ability to accumulate more of the underlying asset for its shareholders, rather than focusing on short-term fiat-denominated price fluctuations.
Question 2: Why did MicroStrategy pivot from issuing convertible debt to preferred equity?
Answer: According to Jain, MicroStrategy evolved its strategy because perpetual preferred equity is a superior financial instrument. Unlike convertible debt, which was restricted to institutional buyers (144A) and had maturity dates, preferreds can be perpetual, are SEC-registered securities tradable by retail investors on NASDAQ, and offer greater liquidity and more efficient price discovery.
Question 3: How does using leverage allow a Bitcoin treasury company’s stock to trade at a premium?
Answer: Jain explains that intelligent leverage is the key to justifying a premium to Net Asset Value (MNAV). By borrowing at a cost lower than Bitcoin’s expected appreciation, the company can systematically increase its Bitcoin per share over time. He argues that this projected future growth in the underlying asset per share gives investors a reason to pay a premium for the stock today.
Question 4: What is STRC (“Stretch”) and why is it considered a “game-changer”?
Answer: Jain describes STRC as a short-duration, high-yield perpetual preferred security. It is engineered to provide a stable price and a high dividend, stripping out the price volatility of Bitcoin. He calls it an “iPhone moment” because its simplicity and focus on yield make the benefits of a Bitcoin-backed asset understandable and attractive to a much broader audience, such as retirees and income-focused investors who cannot stomach volatility.
Question 5: What was the reasoning behind MicroStrategy issuing public guidance on its stock issuance (ATM) strategy?
Answer: Jain reveals that the company decided to provide a clear, rules-based framework for its At-The-Market (ATM) equity issuance to increase transparency and combat negative sentiment. The guidance specifies at which MNAV multiples they will or will not issue shares to buy Bitcoin, giving investors and traders more confidence and clarity, while disarming short sellers who previously capitalized on uncertainty.
Question 6: Why is Wall Street’s increasing involvement considered a major turning point for Bitcoin?
Answer: Jain argues that Wall Street’s involvement is a massive deal because their fundamental incentives have now shifted in favor of Bitcoin. He points out that major banks are now generating substantial fees from distributing Bitcoin-backed securities like MicroStrategy’s. Since banks always follow the money, they are now financially motivated to support and promote the Bitcoin ecosystem, turning them from skeptics or adversaries into powerful allies in the “war on capital.”
People and Organizations Mentioned
- Joe Burnett: Host of the Mustard Seed podcast and associated with Semler Scientific, another public company that has adopted a Bitcoin treasury strategy. (@IIICapital)
- Chaitanya Jain (CJ): Member of MicroStrategy’s Bitcoin treasury team. (@_ChaitanyaJ)
- Strategy (MicroStrategy): The publicly traded software company, pioneered by Michael Saylor, that was the first to adopt a Bitcoin treasury reserve strategy in 2020. (strategy.com)
- Michael Saylor: Executive Chairman of MicroStrategy and a prominent Bitcoin advocate, widely regarded as the architect of the corporate Bitcoin treasury strategy. (@saylor)
- Sharish Jajodia: Corporate Treasurer and Head of Investor Relations at MicroStrategy; CJ’s manager.
- Charlie Madden: Director of Capital Markets at MicroStrategy.
- Bhakti: Junior Analyst on the MicroStrategy treasury team.
- Ella Hough: A new member joining MicroStrategy’s Bitcoin advocacy team. @21MMforthe21st
- Semler Scientific (Semmler): The company Joe Burnett works for, which recently announced its own Bitcoin treasury strategy, following in MicroStrategy’s footsteps.
- Phong Le: President & CFO of MicroStrategy.
- Andrew Kang: Former CFO of MicroStrategy, now on the board of directors.
- Jesse Meyers: A financial analyst known for creating a popular chart illustrating the size of various global asset classes, often used in Bitcoin discussions to show its potential market size. @Croesus_BTC
- Pierre Rochard: A long-time Bitcoiner and analyst, mentioned for his blog post on the “Speculative Attack” concept as it applies to Bitcoin. (@pierre_rochard)
- Paul Krugman: A Nobel prize-winning economist whose work was cited as a possible origin for the “speculative attack” theory.
- Harvard Business School: The institution from which CJ recently graduated with an MBA.
- Harvard’s endowment: The university’s massive investment fund, which was recently disclosed to have purchased over $100 million worth of a spot Bitcoin ETF.