Last week I mentioned a Bitcoin thesis that fell through. I’ll walk through the timeline and how everything went down.
October 6, 2025: the top. Bitcoin hit its all-time high of about $126,200 on October 6, 2025. It spent the next eight months going down. By early June 2026 it was trading in the high $60Ks, more than 45% below that peak.
Early June 2026: the hunch. Somewhere in there I realized I’d stopped seeing Bitcoin on my social feeds. Nobody was arguing about it anymore. To me, that silence felt like what a local bottom sounds like. It was a hunch, nothing more.
The popular hypothesis. Then I ran into an argument built on the four-year halving cycle. In past cycles, the bottom had arrived roughly a year after the peak, and a year after October 2025 is October 2026. Analysts were running with it. Benjamin Cowen was projecting a bear market bottom in October 2026, and Ali Martinez was calling for $38,000 to $50,000.
Two problems. First, the sample size is tiny. A few cycles can’t prove a pattern. Second, and worse, this wasn’t a contrarian view. It was the consensus. Popular retail opinions scare me, because the more crowded a strategy gets, the less it works. I didn’t know what to do with that, so I did the boring thing: mark some dates on the calendar and wait to see whether it would really bottom.
June 8: the plan. I wrote down what I’d need to see before buying:
Price at or below $50K
ETF flows stabilizing or turning positive
Rate and Fed sentiment shifting toward cuts
My exit was half at $108K to $115K, with the rest riding toward a gold-parity ceiling. I set calendar reminders for mid-September and early October.
Late June through July: nothing. Bitcoin slid into the high $50Ks, then drifted back through the $60Ks. There was some ETF flow stablization, but the price and rate sentiment were off. The plan said wait, so I waited.
August: the bottom moved. Bitcoin dipped to roughly $63K in mid-August and then ripped. Spot ETFs took in $3.52 billion in August, up from $172 million in July, and Bitcoin gained about 25% in the month. On August 25 it passed $80,000 for the first time since mid-May, helped along by a record short squeeze. Notably, it wasn’t a Fed cut that did it. It was flows and forced buying.
By then my price condition had failed in the wrong direction. Bitcoin wasn’t falling toward my $50K. It was ripping away from it, so whatever August was, it wasn’t a low I could have bought. What bothered me more was that I couldn’t explain it. The thesis I’d been watching hadn’t played out, and I didn’t understand what was happening instead. That discomfort sent me looking for answers.
Why the bottom came early. After a short conversation with Claude, I realized this is a known pattern across asset classes. When everyone believes they know when the bottom will occur, it tends to occur before that date. Everyone expects a pile-in at the bottom, which makes the bottom hard to time, so people buy early. All that early buying erases the bottom they were waiting for.
I had even spotted the crowding problem in advance, but didn’t know what the effects would be. Now I do. Regardless, I still built a plan whose entry was calibrated to the crowd’s date.
Where I am now. $82,516.17. By late September, ETF inflows had hit their highest levels of 2026, and Bitcoin was holding near $85,000. It never touched $50K. I have no position.
The harder problem: no anchor. With Salesforce or Lennar, I can estimate what the business is worth and wait for a discount. Bitcoin has no cash flows and no intrinsic value to anchor to. All of its value comes from perspective. To understand it, you have to model demand and adoption, which is what I should have been doing instead of watching a calendar.
Modeling demand. Three forces matter most to me:
Institutions. Most of the real adoption story now is institutional. That’s a tailwind, but a slow one.
The speculators left. The get-rich-quick and gambling crowd that fueled earlier cycles has largely been siphoned off by the AI hype machine. That hurts long-term adoption.
Cheap money is gone. With rates and inflation high, people are feeling the pinch. Speculative assets get inflated by easy money, and there’s less of it around.
Where that leaves me. I think Bitcoin likely bounces when the rate environment eventually changes. I just don’t know when that happens, and neither does anyone else. I’m already making a rate bet with Lennar, so I don’t need a second one that depends on the same macro turn and has no value anchor.
What I took from it. I didn’t get the bottom I was waiting for, and I still don’t fully understand why. But I don’t think the plan was a mistake. When you don’t know what you’re doing, there’s nothing wrong with forming a hypothesis, writing down what would confirm it, and waiting. That’s cheap, and it kept me from buying on a hunch.
What it cost me was a trade I never made. What it gave me was a better question. I started the summer asking when Bitcoin would bottom, and I ended it asking what actually drives demand for something with no cash flows. I’d rather be wrong about the first one and learn the second.
Happy investing.
