Creator of Bitcoin valuation framework used by @saylor | past: Stanford MBA, Bain & Co

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This is my 3rd Bitcoin bear market. Here's what seems clear to me, that newer Bitcoiners may not feel.... 1. This is what a BTC bear market bottom feels like Normie friends have been asking me "is BTC going to be 60s forever?" and "what positive catalysts are on the horizon?" One of the big lessons I've learned in BTC cycles is that the tops feel bullish... and the bottoms feel bearish. The end of a bear market is primarily a function of running out of sellers. The bearish sentiment builds on itself and shakes out low conviction holders... until you exhaust potential sellers. Or perhaps a more precise mental image... the bottom is in WHEN the pile of capital hoping for a lower entry price to buy BTC has become disproportionately large relative to remaining potential sellers. A BTC bear market doesn't end because good news arrives. It ends because bearish momentum can't be sustained and naturally ebbs. Then, suddenly, people sitting in cash are caught offsides and must bid BTC higher as they try to get back in. 2. The 2022 cycle bottom felt similar June 2022, it felt like shit watching BTC tumble below prior cycle high ($20k) for the first time ever. Price tumbled from $30k to $18k in a few days. People thought we were headed to $12k . In hindsight, that was peak bearish momentum. Over the next ~5 months, BTC drifted lower, with FTX fallout setting a cycle low in November at $15.5k . BTC felt gloomy and quiet for 2 months... and then popped back to $23k in January 2023 all of a sudden. In hindsight, that was the start of a 2.5 year bull market that took BTC to $126k, roughly ~8x from cycle low. 3. Metrics show 2026 repeating the psychology of 2022 This chart shows Short-Term Holder cost basis (pink line) and how it tracks with BTC market price (white line). The bottom half shows this as a ratio between the two numbers (STH MVRV). Credit to @_Checkmatey_ for this excellent chart. In the 2022 bear market, you can see that the lowest STH MVRV ratio was June 2022. After this point, Short-Term Holder cost basis drifted lower along with BTC price for ~7 months, until January 2023 when BTC jumped convincingly above the pink line for the first time in 13 months... and a new bull market had begun. In 2026, the MVRV ratio spiked lowest in Feb. Since then, STH cost basis and BTC price have drifted lower for ~6 months now. 4. What this could mean for BTC's near future If the parallels between 2022 and 2026 continue, it would mean BTC price jumping convincingly above STH cost basis sometime in the next few months. (7 months post peak bearish momentum would mean September 2026; 13 months below STH cost basis trendline would mean November 2026.) And in hindsight, that breakout moment could be the start of a 2.5 year bull market. (8x from $58k low would be $464k, but even a 4x would be $232k/BTC.) If history repeats, this was the bottom. And in 4 years, you'll look back at $64k BTC the same way we now look back wistfully at $19k BTC.
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Jesse Myers retweeted
The era of always-on capital markets is here. Daily dividends, 365 days a year.
Strategy is proposing daily dividends on $STRF, $STRC, $STRK, and $STRD, accruing every calendar day, including weekends and holidays, and paid the next business day, with economics unchanged. The proposed changes aim to support price stability, liquidity, and demand.
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Jesse Myers retweeted
My thoughts on why the rejection of CLARITY marks a positive inflection point for Digital Assets, and why supportive rules and free markets should now accelerate innovation and growth.
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All of this ended up happening
STRC down to $82.6 today. Here's my read: 1. Strategy is fine. If everything stays as is, they can pay STRC dividends for 32 years. If BTC appreciates at ~2% CAGR, they can pay dividends indefinitely. 2. Why the sell-off? This appears to be a liquidation cascade. Over the last 6 months, the narrative became that STRC volatility was reducing, and price began to spend all its time in $99-100 range. This invites leverage. If you expect the price to always be north of $95, you can take on 20x leverage with your portfolio to buy more STRC and dramatically increase the yield on your portfolio. This works great, until it doesn't. STRC is designed as a free-market asset. When attention shifted to SATA and STRC price flagged, it may have raised the attention of opportunistic short-selling hedge funds. By shorting aggressively, they could push the price down and start triggering margin calls and liquidations from folks who aggressively levered up their STRC positions. The price action today is a clear liquidation cascade, rapidly pushing prices lower, in turn triggering additional liquidations. 3. What happens now? The market will heal itself. Opportunistic hedge funds will recognize that this is a firesale and the fundamentals are unchanged for STRC and step in as buyers. Shorts will close, becoming buyers. Individuals are getting a tremendous entry price for long-term holding STRC shares. Buyers at this level will get ~13.7% effective yield. If STRC trades back to $100 and they sell, they get an easy +18% return. 4. What will Strategy do? Strategy will likely increase the dividend rate on June 30 - maybe to 11.75% but possibly to 12%. Buyers at the current price level then would get 14.2% effective yield from that point forward. Strategy may also step in to buy STRC shares back. They could do this by issuing new shares of MSTR (currently at 1.14 mNAV) or by taking on traditional debt and deploying those funds to buy discounted STRC shares on the market. If/when STRC trades back to $100, Strategy could then re-issue those STRC shares. The ~$15 delta per share could be used to buy BTC as pure accretion to MSTR holders, with no net change to amplification. No doubt that Saylor has already at least considered this, and it wouldn't surprise me if they're currently doing this. 5. In summary... The market is freaked out that this depeg is like Terra/Luna... but this is not an asset like that. Strategy's balance sheet determines whether STRC continues to receive dividend payments... and Strategy's balance sheet is completely unchanged. This is a leverage wipeout. From this, the market will learn that Digital Credit is mostly very low volatility. But because it is a free market asset, the longer that a Digital Credit instrument trades within a tight range to par... the more leverage will inevitably pile up as people get greedy. And that creates the conditions for a leverage wipeout depeg. Following that, the instrument will make its way back to par value as the market heals itself and recognizes that the dividend payments will continue uninterrupted because the issuer's balance sheet is unaffected.
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Jesse Myers retweeted
The SEC’s innovation exemption enables 24/7 onchain trading of tokenized $STRC and $MSTR for U.S. investors through qualifying venues. A major breakthrough for Digital Credit and American capital markets.
🚨 TODAY: The SEC issued an order granting temporary, conditional exemptive relief to Tokenized Securities Venues from the definition of “exchange” in the Exchange Act to trade tokenized NMS stock using innovative permissioned automated market makers and liquidity pools.
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Jesse Myers retweeted
With CLARITY stalled, I expect the SEC, CFTC, and Treasury to advance rules under existing law, banks to expand Bitcoin custody and loans against it, and more capital to favor Bitcoin and digital credit. GENIUS supports stablecoin adoption. Progress need not wait for Congress.
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It's time to think about the 2028 halving and what it could mean for BTC price. As of now, only 1.6 years until the next halving. After prior halvings: - 2012: ~100x rally over 12 months - 2016: ~30x rally over 18 months - 2020: ~8x rally over 18 months The halving has been the quadrennial heartbeat of Bitcoin's marketing and monetization. But in 2024, something different happened. The pattern of halving --> bull market was already established enough that people front-ran the halving. For the first time, we had a new all-time-high before the halving. - 2024: ~4x in 18 months BEFORE halving, ~2x rally over 18 months after halving So what will happen this cycle? Nobody really knows, but I think the precedent has been established to front-run the halving. That's the game theory now. If the same pattern plays out this cycle, the next 1.6 years could be the most explosive time for BTC. Repeating the prior cycle would look like: - 4x over 1.6 years: $58k (recent bottom) --> $232k at April 2028 halving - 2x over 18 months after halving: $232k --> $464k in 2H 2029 BTC could certainly deliver diminishing returns vs the prior cycle (as it has tended to do), but at some point that trend breaks to the upside. The key point for now is that people are likely to front-run the halving. And that could make the next 1.6 years the most exciting part of this Bitcoin cycle.
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Early this year, Bitcoin was down while Silver and Gold boomed. Everyone said Bitcoin had failed as a store-of-value asset. Ever since, BTC has quietly closed the gap. At their extremes in Q1 2026: - Gold: +25% - Silver: +63% - Bitcoin: -29% 2026 performance YTD now: - Gold: +3% - Silver: -8% - Bitcoin: -10% I'm betting BTC ends up the best performer for 2026. 4 months to go!
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Jesse Myers retweeted
Bitcoin may have just begun a 2-3 year bull market. Here's why, and what that could mean for BTC price. 1. BTC has decisively popped above Short-Term Holder cost basis (pink line) Three weeks ago (at $64k), I said we were at the bottom. I noted that a decisive jump above the STH cost basis loomed in the coming months, and it happened a bit faster than expected! It seems that many don't see the latest rally as persuasive evidence of a major trend change. For me, this chart from @_Checkmatey_ tells the story... 2. The 2026 bear market has followed a remarkably similar pattern to 2022 In 2022, the ratio of BTC Price to STH cost basis (aka STH MVRV, the orange and blue metric on bottom half of this chart) bottomed in June, then drifted back to neutral for 7 months as the bear trend lost momentum. 7 months later, in January 2023, BTC price jumped decisively above STH cost basis. Then, STH MVRV spent 80%+ of the next 2.5 years in positive territory. All that orange on this chart? That's a bull market. Here in 2026, the STH MVRV ratio bottomed in Feb, then drifted back to neutral for 7 months as the bear trend lost momentum. ~7 months later, in late August, BTC price jumped decisively above STH cost basis. That's where we are now. 3. Welcome to the new bull market If the 2022 bear and 2023-25 bull cycle continue to repeat, we have just begun a new 2.5 year bull market. As I pointed out in my prior post, the start of a new BTC bull market is not a result of good news arriving. Rather, it's primarily a function of the bearish trend running out of steam (and sellers). Right now, what's left are three types of portfolios: those who don't know enough about BTC to want it (yet), those who are happy with their BTC holdings, and those who were waiting to buy BTC lower. Guess which group is watching in pain? In the early bull market, this is the dry powder that will bid BTC upwards as bears capitulate and get back in, one-by-one. This is just the first stage of a bull market. The pendulum of market psychology for BTC has just begun to swing towards the bullish zenith. It will take years to go from disbelief (now), to optimism, to mania. A big part of this process will be the next halving, currently on track for mid-April 2028. New BTC supply issuance will be permanently halved. This causes a supply shock, but more importantly, a marketing narrative for BTC. People will front-run, others will chase. All of that is still ahead. 4. My base case expectations With hindsight, I think this will be viewed as the start of the 2026-29 bull market. I think we will spend 80%+ of the next 2.5 years with BTC price above the STH cost-basis (pink line). How high this bull market goes is harder to say. The last bull market delivered an 8x from the bear-market low. An 8x from this bear-market low ($58k) would be $464k, but even a 4x would be $232k/BTC. If you thought Bitcoin was dead, or you were hoping to buy BTC lower... now might be the time to re-evaluate.
This is my 3rd Bitcoin bear market. Here's what seems clear to me, that newer Bitcoiners may not feel.... 1. This is what a BTC bear market bottom feels like Normie friends have been asking me "is BTC going to be 60s forever?" and "what positive catalysts are on the horizon?" One of the big lessons I've learned in BTC cycles is that the tops feel bullish... and the bottoms feel bearish. The end of a bear market is primarily a function of running out of sellers. The bearish sentiment builds on itself and shakes out low conviction holders... until you exhaust potential sellers. Or perhaps a more precise mental image... the bottom is in WHEN the pile of capital hoping for a lower entry price to buy BTC has become disproportionately large relative to remaining potential sellers. A BTC bear market doesn't end because good news arrives. It ends because bearish momentum can't be sustained and naturally ebbs. Then, suddenly, people sitting in cash are caught offsides and must bid BTC higher as they try to get back in. 2. The 2022 cycle bottom felt similar June 2022, it felt like shit watching BTC tumble below prior cycle high ($20k) for the first time ever. Price tumbled from $30k to $18k in a few days. People thought we were headed to $12k . In hindsight, that was peak bearish momentum. Over the next ~5 months, BTC drifted lower, with FTX fallout setting a cycle low in November at $15.5k . BTC felt gloomy and quiet for 2 months... and then popped back to $23k in January 2023 all of a sudden. In hindsight, that was the start of a 2.5 year bull market that took BTC to $126k, roughly ~8x from cycle low. 3. Metrics show 2026 repeating the psychology of 2022 This chart shows Short-Term Holder cost basis (pink line) and how it tracks with BTC market price (white line). The bottom half shows this as a ratio between the two numbers (STH MVRV). Credit to @_Checkmatey_ for this excellent chart. In the 2022 bear market, you can see that the lowest STH MVRV ratio was June 2022. After this point, Short-Term Holder cost basis drifted lower along with BTC price for ~7 months, until January 2023 when BTC jumped convincingly above the pink line for the first time in 13 months... and a new bull market had begun. In 2026, the MVRV ratio spiked lowest in Feb. Since then, STH cost basis and BTC price have drifted lower for ~6 months now. 4. What this could mean for BTC's near future If the parallels between 2022 and 2026 continue, it would mean BTC price jumping convincingly above STH cost basis sometime in the next few months. (7 months post peak bearish momentum would mean September 2026; 13 months below STH cost basis trendline would mean November 2026.) And in hindsight, that breakout moment could be the start of a 2.5 year bull market. (8x from $58k low would be $464k, but even a 4x would be $232k/BTC.) If history repeats, this was the bottom. And in 4 years, you'll look back at $64k BTC the same way we now look back wistfully at $19k BTC.
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Jesse Myers retweeted
Sorry to see this, Jesse. You were writing the intellectual foundation of this sector years before most treasury companies had a ticker. People who understand both Bitcoin and capital markets are the scarcest asset in this industry. Wishing you every success in the next chapter.
I’m sad to say my time at The Smarter Web Company has come to an end. I joined SWC because I believed there was an opportunity to help build something genuinely important in the Bitcoin treasury space. I’m proud of the role I played in helping shape the company’s Bitcoin strategy and its evolution over the past year. In recent weeks, it became clear that SWC leadership and I had different views about my role and what a long-term working relationship should look like. We weren’t able to resolve those differences, and ultimately my employment was terminated. The company’s announcement states that “Jesse Myers is leaving the Company.” For clarity, I did not resign; my employment was terminated. For additional context, my termination follows the departures of the other two senior executives who reported directly to the CEO in March. I’m very disappointed by the outcome, but remain proud of what we built and of my role in helping shape the future of Amplified Bitcoin in the UK. I remain optimistic about Smarter Web’s prospects as the UK’s leading Bitcoin treasury company, and continue to be very excited about the future of Bitcoin treasury companies globally. One of the best parts of my time at Smarter Web was working alongside an exceptional group of people across the team. I have tremendous respect for them and wish them every success. I’m also deeply grateful to the remarkable community of shareholders who supported Smarter Web and encouraged me personally along the way. It has meant a great deal to me, and I sincerely wish them well.
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I’m sad to say my time at The Smarter Web Company has come to an end. I joined SWC because I believed there was an opportunity to help build something genuinely important in the Bitcoin treasury space. I’m proud of the role I played in helping shape the company’s Bitcoin strategy and its evolution over the past year. In recent weeks, it became clear that SWC leadership and I had different views about my role and what a long-term working relationship should look like. We weren’t able to resolve those differences, and ultimately my employment was terminated. The company’s announcement states that “Jesse Myers is leaving the Company.” For clarity, I did not resign; my employment was terminated. For additional context, my termination follows the departures of the other two senior executives who reported directly to the CEO in March. I’m very disappointed by the outcome, but remain proud of what we built and of my role in helping shape the future of Amplified Bitcoin in the UK. I remain optimistic about Smarter Web’s prospects as the UK’s leading Bitcoin treasury company, and continue to be very excited about the future of Bitcoin treasury companies globally. One of the best parts of my time at Smarter Web was working alongside an exceptional group of people across the team. I have tremendous respect for them and wish them every success. I’m also deeply grateful to the remarkable community of shareholders who supported Smarter Web and encouraged me personally along the way. It has meant a great deal to me, and I sincerely wish them well.
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Jesse Myers retweeted
7/ And it's still a small fish. Like... really small. Bitcoin: roughly $1.27 trillion. Global wealth: $1,127T H/T @Croesus_BTC
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Jesse Myers retweeted
Bitcoin has underperformed almost every major asset in 2026. Meanwhile, hash rate has been declining for ~10 months, the most prolonged mining contraction in Bitcoin’s history. I think the two are connected.
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Jesse Myers retweeted
We talk a lot about the "coming wealth transfer" as Boomers age and what that means for investments. But what if the "wealth" is in things the next generation either does not value or can't maintain, such as art? This recent article from Bloomberg notes: "The sheer tonnage of boomer-owned art is vast, and the total demand for it doesn’t come close to the amount of supply that’s about to arrive." [1] Furthermore, it may be hard for the next generation to store it properly, enjoy it, or show it. I'm reminded of the "Bitcoin Total Addressable Market" from @Croesus_BTC that he recently updated: nitter.siddz.com/Croesus_BTC/status/207…
2026 update - Global Asset Landscape Global asset value +11% in the last year, now $1,127T. Expand THREAD to see which categories grew / shrank.
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Smarter Web Livestream: Friday, 15:30 GMT / 11:30 EDT. Jesse Myers (@Croesus_BTC), Head of Bitcoin Strategy at Smarter Web, is joined by Sam Callahan (@samcallah), Director of Strategy & Research at OranjeBTC (@ORANJEBTC) - the largest Bitcoin treasury company in Latin America, holding 3,950 BTC. The conversation will explore how the treasury model is taking shape across different markets and regulatory environments. LSE: #SWC | OTCQB: $TSWCF | FRA: $3M8
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The reason that Bitcoin treasury companies are interesting is that they have the potential to grow BTC ownership over time. This can be achieved two ways: 1. Accretive equity transactions that grow Bitcoin per share (e.g., issuing shares at premium to NAV, discounted share buybacks, etc.) 2. Amplification playing out favorably and delivering a growth in Net Bitcoin per share Not all BTCTCs will achieve positive results, and there is risk inherent in this playbook. But, Strategy grew Bitcoin per share by ~74% in 2024 and ~23% in 2025. If a BTCTC averages 20% growth in Bitcoin per share per year for 5 years, its shareholders will have grown their effective BTC exposure by ~2.5x. This is how we are thinking about the potential for Smarter Web @smarterwebuk and what we aim to deliver for shareholders. In my opinion, cold storage BTC should be a part of everyone's portfolio. But if there's a place for risk in a portfolio, then well-run BTCTCs trading at a discount to NAV are compelling.
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Jesse Myers retweeted
New chart: MVRV Quantile Bands Bitcoin is currently in the lowest 10% sector. Zoom out, we are close to a bottom here 👀
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