One of the most popular questions we received in our latest subscriber Q&A asked how high Bitcoin may run in the next bull market.

It is obviously impossible to answer this question with any accuracy, but that doesn’t mean we can’t make a reasonable effort to model it out, and indulge in a little speculation.

Today’s post is going to give us a break from the bear market, and instead run an analysis to punt on where the next Bitcoin cycle high may be.

One day, we will of course hit the price I identify in this piece, at which point I will drop the paywall and gloat on twitter saying ‘see, we called it!’.

Time to speculate on the number go up technology that Bitcoin is.

Become a Premium subscriber to access today’s Video Update (25 mins), Written Article and TL;DR Summary.

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We’re back with our monthly discussion between from and James about all things Bitcoin and macro.

In this conversation, James starts out with the key onchain and technical charts he is using to navigate this bear market. We analyse how our interpretation of onchain cohorts must evolve as the market cycle progresses and investor sentiment changes season.

Nik then explains why the strengthening US dollar, particularly against key Asian currencies, is coming increasingly to the foreground. Interest rates, oil prices, and equity market wobbles are on his radar, but the strength of the king dollar is what he believes should be commanding our attention right now.

Paid subscribers will find the discussion between Nik and James below.

Become a Premium subscriber to access today’s Video Update (1hr).

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Buy high and sell low, it’s age old wisdom that stands the test of time.

The higher the price you buy, and the lower the price when you sell, the larger the loss, and the better your overall net worth will be in the long-run.

The 2026 bear market has been so ruthless, that even the most Diamond handed dude Michael Saylor has sold 3,588 BTC at the basement bargain price of $60k.

All jokes aside, there is both rhyme and reason to what Strategy is doing, and the market has responded relatively well given ‘the only buyer’ has turned into a seller.

Makes you wonder, as all the critics have been saying that Saylor is the only dude who has been buying Bitcoin…if he’s now selling…who on earth is buying?

Upgrade below to access today’s Video Update (33 mins), Written Article and TL;DR Summary.

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Thanks to our Premium subscribers for another fantastic batch of questions this month!

In this Q&A session, James and Alec cover everything from bull market targets and cycle theory to Strategy, BIP-110, and where we think this market is headed, including:

• Next bull market upside from a $50–60k bottom

• Is the four-year cycle still intact?

• Does the data support a $40k BTC bottom?

• Is Strategy’s capitulation phase almost over?

• James’ view on BIP-110

• What would make us turn bullish?

• Where do we expect Bitcoin to bottom?

• Are long-term holders still selling?

• Are diminishing returns the new reality?

• James’ favourite research sources

We hope you enjoy the session,
James & Alec

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We had a great call today, covering key slides from our latest Bitcoin Monthly Report. Big thanks to all the attendees and those who raised their hands to participate in the session, we highly value your input!

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The last month has been a chaotic one for the Bitcoin market, with prices setting a marginally lower low at $58k, and with a significant break-down in Strategy’s preferred and common stock prices.

These are the dynamics one would expect to see in a late stage bear, and despite the apparent headwinds, downside momentum seems to still be waning.

In this month’s Orange report, I present a set of models and ideas to reason about what this late stage of the bear may look like. I also provide an assessment of the position Strategy is in, and reflect on their latest updated framework for how they plan to manage their balance sheet.

Orange Members will find the report PDF, and details of our upcoming monthly conference call below.

Note: This monthly report & upcoming conference call is exclusive to Checkonchain Orange subscribers - which is our upper-tier plan within Substack.

If you would like to learn more about Orange, or access a single monthly report + conference call recording, please click the button below.

Learn More About Orange Plan

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For those who were not around last cycle, there was an army of folks who bought their first slugs of Bitcoin around $58k during the two rounded tops in the 2021 bull cycle.

Folks who top blasted $58k in the last cycle wear their buys as a badge of honour, and rightfully so. They survived the brutal decline of the 2022 bear, and learned a tonne of lessons about themselves along the way.

It is a tremendous life experience to watch your net worth plummet by over -70%. It forces you to either come to terms with what you own and why through rigorous study…or to capitulate everything when the pain gets too much.

Here we are, five years later and the $58k gang rides once again.

As you can probably imagine, the market conditions at $58k in 2026 are vastly different to those at the stimulus fuelled tops in 2021. Today’s report will be an analysis of how the market is reacting to the market probing the bear cycle lows, and why my expectations are in the weeks and months ahead.

Upgrade below to access today’s Video Update and TL;DR Summary.

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Welcome to the June edition of our Q&A, where Premium subscribers can ask (and upvote) questions about the Bitcoin market, onchain analysis, and broader macro themes. We will record and publish the Q&A session later this week!

🔍 How To Ask Your Question

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There is a lot happening right now, both from a macro perspective, but also within Bitcoin, as Strategy’s digital credit instruments get whacked lower once again.

I’m going to get right into the analysis today for paid subscribers.

I’ll cover the macro landscape, the negative market impact I believe Strategy is currently imposing, and how I am thinking about Bitcoin as it trades below $60k.

Upgrade below to access today’s Video Update (42 mins), Written Article and TL;DR Summary.

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The Bitcoin market is dead quiet.

No price movement.

Cyclically low trade volumes.

Sentiment in the absolute gutter.

Absolutely nothing is happening, and the market is in a state of total and complete apathy.

These are the conditions we historically see as we approach the pointy end of a bear market, where hopelessness peaks, and the maximum number of people start to truly believe the asset is never coming back.

Today’s post will be an assessment of the current market setup, and how I am thinking about what I suspect will end up being the last major chapter of this bear.

Upgrade below to get today’s Video Update (32 mins), Written Article and TL;DR Summary.

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I wake up to see this ugly-ass looking chart of an asset which is supposed to trade at $100, on low volatility.

Strategy’s preferred stock Stretch (STRC) has taken a nose-dive, which rightfully has many questioning whether this is the market sending a more damning signal.

Today’s post will specifically focus on my thoughts around Strategy (MSTR), and this break-down in their preferred stock prices.

I will also share what impacts this has on my current and future allocations to Strategy related assets, as I have made a few decisions in recent weeks, which this event only works towards cementing.

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Very rarely does the absolute value of a metric matter as much as its rate of change.

Both the financial media, and the twitterazzi love quoting some magic metric that has hit some special new level that explains everything that happened that day. In my experience, what actually matters is how quickly it got there, and whether it is in the process of speeding up, or slowing down.

Late stage bear markets feel like they just drag on…and on…and on….

The monthly chart is red, the weekly chart is red, and the daily chart is red.

However, every day that the gears on this pain-factory grind forwards, the capitulation process works its way through more and more of the folks that only destiny knows will ultimately sell the cycle bottom in disgust.

What remains at the end of this gruelling process, is a hardened holder-base of tenured HODLers, who know exactly what they own, and why they own it.lllllll

The headlines continue to say that Bitcoin is in a deep bear market, with many pundits expecting it has much further to go. The absolute values which measure this bear market, are certainly quite bearish.

What really matters, is the rate of change, and to my eye it is starting to tell a different story.

Become a Premium subscriber to access today’s Video Update (49 mins) and TL;DR Summary.

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Today we have a double header for you, with two analysis videos covering both the Bitcoin onchain and macro landscape.

1. Bitcoin onchain update with James, where we explore the record share of Bitcoin supply now held by Long-Term Holders, visualise how the supply structure has changed since the February capitulation event, and assess whether the recent sell-off has the hallmarks of a classic time-pain capitulation event.

2. Macro update with Nik Bhatia & James. In this discussion, we cover both the acceleration in AI CAPEX wave, why strength in the US Dollar is a warning shot for risk assets, and why Nik thinks of Scott Bessent as the ‘Secretary of Volatility’.

We’re in the phase of the bear market where the maximum number people drop off, driven away by severe boredom, frustration, and a lack of the requisite patience.

Markets that reach this apathetic stage tend to also be near their point of maximum opportunity, but only those with the grit to see the end of the movie are around to enjoy it.

Become a Premium subscriber to access both of today’s Video Sessions and the TL;DR Summary.

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It’s a grueling process, surviving a bear market.

It’s especially hard when AI tech stocks are ripping higher, and are sucking all the capital oxygen out of the room. The parabolas envy is real, and has been a major theme in markets over the last 12 to 18-months.

As discussed in Peak Apathy, we’re at the stage of this bear market where nobody…absolutely nobody cares about Bitcoin.

At the same time, we’re starting to see some very interesting divergences in how investors are behaving. Many of these divergences were last seen around the ass-end of the prior bear cycle.

Time-pain has the effect of flushing out all the folks who don’t have the conviction to see the end of the movie.

Today’s note will be an analysis of these divergences, and my updated expectations for both the short, and medium term prospects for the orange coin.

Become a Premium subscriber to access today’s Video Update (39 mins), Written Article and TL;DR Summary.

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Resilience is about how quickly you can rebound from a shock event, and begin thinking and processing your next decisions clearly.

There is a huge swathe of the Bitcoin holder base, who are currently in a state of shock, fear, panic, and totally unable to collect their thoughts.

We have all been there, and the lesson we usually learn is that when we make decisions based on our emotions, it almost always leads to our biggest mistakes.

One of my subscribers asked me a question last weekend, which I believe is the perfect one to answer for today’s post. To paraphrase the question:

I know buying Bitcoin via a dollar-cost-average (DCA) campaign helps with the emotions of investing. However, it is very hard to know how long that DCA campaign should run for.

In the context of a Bitcoin holder with a pile of cash, should I seek to lump sum near the bottom, or is there an ideal DCA strategy that I could employ, and for how long?

This is the perfect topic to address for breaking us out of the shockwave of the sell-off, and put some numbers and context to the execution step.

Today’s note will compare how the lump sum vs DCA strategy has performed through previous Bitcoin bear markets, with a focus on putting the probabilities in our favour.

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I’d like to welcome you all to today’s ceremony, where we will be celebrating the wonderful life that Bitcoin has lived, and the joy it brought to our lives.

We will miss it, but we will never forget it.

It is time for the first eulogy, please be seated.

Today’s post will be my analysis of this sell-off, how investors are responding to it, and what the probabilities say about prices trading at $66k.

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Strategy just announced that the firm sold 32 Bitcoin for $2.5 Million, making for only the second time their Bitcoin balance has nominally declined (the other was a sale of 704 BTC in Dec-2022).

Saylor sold Bitcoin, and is sending a message in doing so.

In today’s note, I will discuss my views on this event, and what I believe it means for the company moving forwards.

I will also expand on a risk I highlighted in my last appearance on the What Bitcoin Did podcast, where I noted that there is in fact a Bitcoin price where the mathematical value of MSTR stock goes to $0.

Given the tremendous 843,706 hoard of Bitcoin Strategy owns, it is prudent to understand and appreciate the risks that come with it.

Become a Premium subscriber to access today’s Video Update (40 mins), Written Article and TL;DR Summary.

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It is so easy to get swept up in the emotions of each and every daily price candle.

Every bear market headline feels like impending doom.

We’re going so much lower, they say.

The latest green candle brings back just enough hope to make it feel like a recovery is on the table…with the next red candle dashing it, and making the bear feel like it will grind on forever.

Today’s post is all about the tools I use to get rid of these emotions, kick them out the door.

Instead, I focus on putting the accumulation odds in my favour, and ignore the rabble of price predictooors, because they don’t have a crystal ball either.

Become a Premium subscriber to access today’s Video Update (35 mins), Written Article and TL;DR Summary.

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We had a great call today, covering key slides from our latest Bitcoin Monthly Report. Big thanks to all the attendees and those who raised their hands to participate in the session, we highly value your input!

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Bitcoin bear markets tend to end on apathy, often with a painful last flush-out that I call the ‘time-pain capitulation’.

Whilst downside momentum tends to crescendo with the price-pain capitulation event, many more are shaken out by the endless barrage of bad headlines, and endlessly leaky prices. The frustration, boredom, and unwind of all remaining long-bias takes it’s toll…and it takes time to do so.

This month’s Orange report is titled The Time-Pain Capitulation, and is an exploration of the market setup through this period, and some of the key drivers (and perhaps future headlines) that may motivate it.

This report covers four main topics:

• My assessment of the market setup related to the time-pain chapter.

• Onchain, volume and sentiment analysis describing investor apathy.

• A deep dive into ETF outflows and their relation to derivatives markets.

• Risk vectors pertaining to Strategy, MSTR, preferred stocks, and debt.

Orange Members will find the report PDF, and details of our upcoming monthly conference call below.

Note: This monthly report & upcoming conference call is exclusive to Checkonchain Orange subscribers - which is our upper-tier plan within Substack.

If you would like to learn more about Orange, or access a single monthly report + conference call recording, please click the button below.

Learn More About Orange Plan

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