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The Hardest Decision I Make Every Cycle
In December 2017, I watched my portfolio hit a value that represented life-changing money. I had been accumulating since 2013. Bitcoin was approaching $20,000. Ethereum had gone from $8 to over $700. The altcoins I held had done multiples of that. Every day I didn't sell felt like leaving money on the table. Every day I considered selling felt like stepping off a rocket mid-flight.
I sold nothing. By February 2018, that decision had cost me roughly 40% of my peak portfolio value. By November 2018, it had cost me 84%. The failure wasn't that I didn't sell at the exact top. Nobody does. The failure was that I had no framework. I was making a binary decision with a probability distribution problem.
The question is never "should I sell or hold." The question is "at what prices do I sell what percentages, and why those levels specifically." The difference between those two framings is the difference between systematic wealth extraction and emotional wreckage.
Why Price Levels, Not Emotions
The single biggest mistake I see long-term holders make in a bull market is treating the exit decision as a single binary event. Do I sell or do I hold? This framing guarantees regret. If you sell and the price doubles, you feel like an idiot. If you hold and it crashes, you feel like an idiot. You cannot win a binary game against a continuous probability distribution.
The correct frame is scaling. You define price levels in advance. At each level, you sell a fixed percentage. You do this before the market moves, before euphoria sets in, before fear takes over. The levels are not arbitrary. They are based on your entry cost basis, your risk tolerance, your time horizon, and what you have learned from watching previous cycles.
I use a tranched framework now. I did not use it in 2017, which is why I rode the entire cycle up and 84% of the way back down. I built the framework during the 2018-2019 bear market, tested it during the 2020-2021 bull, and refined it through 2022. It is not perfect. Nothing is. But it removes emotion from the hardest decision you will make in any cycle.
The Levels I Use
My baseline framework uses five tranches, each tied to a specific return multiple from my average cost basis. The percentages are not equal. The closer I get to what I consider full valuation, the more I sell. This is the opposite of what emotion tells you to do, which is why it works.
At 2x my cost basis, I sell 10%. This locks in my initial capital. If the position goes to zero tomorrow, I have broken even. Psychologically, this is the most important sale. It converts the position from "at risk" to "playing with house money." The emotional weight of the position changes entirely.
At 3x, I sell another 15%. At 5x, I sell 20%. At 8x, I sell 25%. At 10x or higher, I sell another 20%, leaving me with 10% of my original position as a long-term hold. These are my personal levels. Yours will be different based on your cost basis, your conviction in the asset, and your financial situation. The point is not the specific numbers. The point is that they are defined in advance and executed mechanically.
The 2020-2021 cycle tested this framework in real conditions. Bitcoin went from $10,000 in September 2020 to $69,000 in November 2021. My average cost basis at the time was around $6,500, built over 2018-2020. That meant my 2x level was $13,000, my 3x was $19,500, my 5x was $32,500, my 8x was $52,000, and my 10x was $65,000. I hit every single level except the 10x, which I missed by timing. I sold the final tranche at $58,000 on the way down, which in hindsight was better than waiting for a level that never came.
By the time Bitcoin peaked at $69,000, I had sold 70% of my position across four tranches. I still held 30%. When it crashed to $16,000 in 2022, that remaining 30% hurt, but it did not destroy me, because I had already extracted multiples of my initial capital. The 30% I held was risk I could afford. That is the entire point.
What I Sold Too Early (And Why That Was Fine)
In the 2020-2021 cycle, I sold my first Ethereum tranche at $800, which was roughly 2x my cost basis. Ethereum went to $4,800. I left 6x on the table for that first 10%. It felt terrible watching it run without me. Every instinct told me I had screwed up.
But the math told a different story. That 10% tranche, sold at $800, represented a locked-in gain. When Ethereum later crashed to $880 in June 2022, that early sale looked prescient. More importantly, the existence of that sale gave me the emotional stability to hold the remaining 90% longer. I had taken some profit. I was not riding the position with white knuckles. I could think clearly.
This is the second-order effect of systematic selling that most people miss. Early sales do not just lock in gains. They reduce the emotional load of the position. A 100% position at 5x creates an entirely different psychological state than a 50% position at 5x after you have already banked profits. The latter lets you think. The former makes you reactive.
I have sold too early in every cycle I have traded. In 2016-2017, I sold Bitcoin at $1,200 before it ran to $20,000. In 2020-2021, I sold Ethereum at $800 before it ran to $4,800. In hindsight, those sales look like mistakes. In real time, they were the correct execution of a pre-defined plan. The plan is not designed to maximize theoretical gain. It is designed to maximize realized gain while keeping you emotionally stable enough to execute the rest of the plan.
What I Sold Too Late (And What That Cost Me)
The flip side is harder to admit. In 2017, I sold nothing. I watched Bitcoin go from $1,000 to $20,000 and Ethereum go from $8 to $1,400, and I convinced myself that "this time was different" and that we were in a paradigm shift and that the old rules did not apply. I believed the narrative. I ignored the framework I should have built.
By the time I finally sold in early 2018, Bitcoin was at $11,000 on the way down and Ethereum was at $900. Those were not bad prices in absolute terms. But they represented a 45% drawdown from the peak for Bitcoin and a 36% drawdown for Ethereum. The opportunity cost of not selling systematically at higher levels was enormous.
The lesson was not that I should have sold everything at the top. The lesson was that I should have been selling in tranches on the way up, so that when the top came and went, I had already extracted significant value and could afford to hold the rest through volatility.
In 2021, I executed better, but I still made mistakes. I held one altcoin position too long because I was emotionally attached to the project. It was a Layer-1 protocol I had researched deeply. I believed in the technology. My cost basis was $0.40, and it ran to $3.80, which was 9.5x. According to my framework, I should have sold 90% of it across multiple tranches. Instead, I sold only 50%, because I told myself the fundamentals justified holding more.
That coin is now trading at $0.60. The 50% I held is worth barely more than my cost basis. The lesson, again, is that conviction in fundamentals does not exempt you from taking profit. Maximizing gains in a bull market requires selling things you still believe in, at prices that feel too early, according to a plan that feels mechanical. If it feels comfortable, you are doing it wrong.
The MVRV Framework For Bitcoin
For Bitcoin specifically, I overlay my tranched selling framework with on-chain data, particularly the MVRV Z-Score. This metric compares Bitcoin's market value to its realized value and adjusts for volatility. Historically, an MVRV Z-Score above 7 has marked cycle tops. A score between 3 and 5 has marked the beginning of significant distribution phases.
As of early October 2026, Bitcoin is trading around $81,000 to $86,000, according to CoinMarketCap data. The MVRV Z-Score is hovering in the 3 to 4 range, which suggests we are in a distribution phase but not yet at euphoric extremes. This aligns with what I am seeing in whale behavior. Over the last five months, supply from major Bitcoin holders declined by 290,000 BTC, but accumulation has started again in recent weeks, indicating that whales have temporarily stopped selling.
This is the environment where my tranched framework earns its keep. The market is not in panic. It is not in euphoria. It is in the middle, which is where most of the bull market actually happens. Systematic selling in this phase feels wrong because the price is still moving up and the narrative is still bullish. But this is exactly when disciplined profit-taking builds wealth. You sell into strength, not into panic.
What Could Prove Me Wrong
I do not know where this cycle tops. I do not know if Bitcoin will reach $113,000, as Citigroup projects, or if it will stall here and consolidate for months. I do not know if the macro environment (persistent inflation, geopolitical instability, potential rate hikes) will compress the cycle or extend it.
What I do know is that my framework is probabilistic, not deterministic. If Bitcoin runs to $150,000 and I have sold 70% of my position by $100,000, I will have left significant gains on the table. That is fine. The goal is not to capture every dollar. The goal is to capture enough dollars that I am financially better off, emotionally stable, and still holding a position if the asymmetric upside case plays out over the next decade.
The worst-case scenario is not selling too early. The worst-case scenario is selling nothing, riding the euphoria to a top I cannot predict, and then riding the drawdown back to breakeven or worse. I did that in 2017. I will not do it again.
Why This Matters For The Next Decade
Crypto is the future of money and global transactions. I believe that. I have believed it since 2013, and nothing in the last ten-plus years has changed that view. But believing in the long-term thesis does not mean ignoring the cyclical reality. Bull markets end. They always have. They always will. The four-year Bitcoin halving cycle may be evolving, as I wrote about in previous analysis, but cyclicality itself is not going away.
The investors who build generational wealth in crypto are not the ones who hold through every cycle. They are the ones who systematically extract value in bulls, deploy it in bears, and compound over decades. Taking profit is not betraying the thesis. Taking profit is what lets you stay in the game long enough for the thesis to play out.
In 2035, I expect Bitcoin to be worth significantly more than it is today. I expect Ethereum and a handful of other protocols to be foundational infrastructure for a global financial system that looks nothing like the one we have now. But between now and then, there will be multiple cycles. There will be multiple opportunities to sell high and buy low. The framework I have built is designed to capture those opportunities without requiring me to predict tops and bottoms.
If you are reading this in October 2026 and wondering whether you should sell some of your position, the answer is probably yes. Not because I think the top is in. I do not. But because if you are asking the question, you are feeling the emotional weight of the position, and that weight will only grow heavier as the market moves. Systematic selling removes that weight. It lets you participate in the upside while protecting the downside. It converts paper gains into realized gains, which are the only kind that matter when the cycle turns.
The Takeaway
I have been trading crypto for more than ten years. I have built a substantial portfolio from nothing twice. I have watched that portfolio drop 84% and come back stronger. The single most important lesson I have learned is this: taking profit in a bull market is not about calling the top. It is about defining levels in advance, selling fixed percentages at those levels, and trusting the framework when every instinct tells you to hold for one more leg up.
The levels I use are 2x, 3x, 5x, 8x, and 10x my cost basis, with increasing sell percentages as the multiples rise. The percentage I sell at each level is 10%, 15%, 20%, 25%, and 20%, leaving me with 10% as a long-term hold. These levels are not magic. They are the result of watching three full cycles, making every mistake once, and building a system that removes emotion from the hardest decision I make every four years.
You will sell too early. You will sell too late. You will feel regret either way. But if you sell systematically, according to a plan built before the euphoria set in, you will walk away from this cycle wealthier than you entered it. That is the only outcome that matters.
Frequently Asked Questions
When should I start taking profit in a crypto bull market?
Start taking profit in systematic tranches at predefined price levels based on multiples of your cost basis, not based on emotions or market sentiment. A common framework is selling 10% at 2x, 15% at 3x, 20% at 5x, 25% at 8x, and 20% at 10x or higher. The first sale at 2x locks in your initial capital and reduces emotional pressure. Begin this process as soon as you hit your first predetermined level, even if it feels too early.
How much of my crypto position should I sell during a bull run?
Sell in increasing percentages as price multiples rise. A systematic approach involves selling 70-90% of your position across multiple price levels while retaining 10-30% for long-term asymmetric upside. The exact percentages depend on your cost basis, conviction in the asset, and financial situation. The key principle is selling more at higher valuations, which is counterintuitive but prevents riding gains back to zero in the subsequent bear market.
What is the MVRV Z-Score and how does it help with profit-taking?
The MVRV Z-Score compares Bitcoin's market value to its realized value, adjusted for volatility. Historically, scores above 7 mark cycle tops, while scores between 3 and 5 indicate significant distribution phases. This on-chain metric helps confirm whether systematic profit-taking aligns with broader market conditions. Use it as a secondary confirmation tool alongside your predetermined price-level framework, not as a standalone timing signal.
Why sell in tranches instead of all at once?
Selling in tranches removes the impossible burden of calling the exact top and eliminates binary regret. If you sell everything and the price doubles, you feel terrible. If you hold everything and it crashes, you also feel terrible. Tranched selling captures gains across a range of prices, locks in realized profits progressively, and reduces emotional pressure with each sale. This approach maximizes your ability to execute the rest of your plan rationally as the market becomes more volatile.
Should I sell crypto I still believe in fundamentally?
Yes. Conviction in long-term fundamentals does not exempt a position from systematic profit-taking during bull market euphoria. Bull markets end regardless of how strong a project's technology is. Taking profit allows you to realize gains, reduce risk, and redeploy capital in the subsequent bear market at lower prices. You can retain a small position (10-30%) for long-term asymmetric upside while banking the majority of cyclical gains. Fundamentals win over years, but cycles dominate over months.
