The Hardest Sentence to Say
On September 21, 2026, Bitcoin climbed to roughly $87,400 — an eight-month high, and clear of the May peak near $82,000. For most holders, that was good news. For an analyst who had spent nearly a decade studying Bitcoin's cycles, it meant doing what he called his least favorite part of the job: admitting, in public, that he had been wrong.
"I was wrong and I'm not going to make excuses," Benjamin Cowen said. He didn't point to some other indicator to change the subject, and he didn't fall back on "I'll be right in the long run." For all of 2026 he had argued that Bitcoin would struggle to take out the May high; that August, he put the odds that the low was not yet in at 65%. The market didn't wait for him.
It wasn't the first time, he said. "I've been loved by the world. I've been hated by the world." The older he gets, the less he wants to be known by the world at all. And then he added one more thing: the people who got it right probably deserved the audience's attention more than he did.
A Window That Lasted Five Days
What stings usually isn't being wrong about direction — it's what being wrong costs you. Cowen's plan for 2026 was simple: once July arrived, start buying as soon as his risk metric fell below 0.3. That condition did arrive. In June, Bitcoin broke below $60,000 for the first time in a year and a half, bottoming near $57,000. But the low-risk zone lasted about five days.
From there Bitcoin rallied hard, and by September 21 it was up roughly 50% from its early-July low. That was his biggest regret. "I guess that goes to show you when the opportunities arise to take more advantage of them," he said. "Because 5 days was obviously not a very long time."
That's worth pausing on. The risk metric is the core of the dynamic DCA framework he built around 2020: invest more when risk is low, less when risk is high. For those five days, the system flashed green. The tool didn't fail. What got in the way was a second voice in the head of the person meant to act on it — the price is going lower, a better entry is still coming.
Being Right and Making Money Are Not the Same Thing
A few days later, with the emotion settled, he came back to it — and the tone had shifted. He reached for a line he has repeated for years: "I'd rather be rich and wrong than poor and right."
"I'd rather be rich and wrong than poor and right."
Calling the market and growing your money are two separate tracks. His bearish view was wrong, but the approach he had been recommending all along — keep dollar-cost averaging through the second half of a midterm year — worked out fine for anyone who actually followed it. He picked up some Bitcoin near the lows himself. Far less than he wanted, but at least, as he put it, he could console himself with the small amount he did get.
He also reworked how he read the market. For the nine months before, every rally had stalled at a lower high, so the burden of proof sat with the bulls: show why this bounce is any different. This time Bitcoin didn't just break the May high — it closed a week above it. That flips the burden to the bears, who now have to explain why it should fall. It doesn't rule out a drop. It just means the old position has to be set down first.
Then he asked the more fundamental question: once you realize you've been wrong, how do you move forward? "As investors we all will face that challenge at some point or another."
What He Learned From the S&P 500
Cowen answered with his own S&P 500 habit. Every month, for years, he has bought low-cost index funds. Now and then he tries to get clever: he normally buys at the start of the month, but if he senses a correction coming, he waits until the end. The results have been mixed — some months he feels like a genius, other months he wishes he hadn't waited. Over time he noticed that what he gained by occasionally being right was offset by the gains he missed when he was wrong, so he drifted toward simply buying early in the month.
That's also why he rarely talks about the S&P 500. His strategy there is to "mindlessly DCA it every month of my life." He knows drawdowns will come, and he'll discuss them, but he almost never sells because of them.
The same person who can set forecasts aside with the S&P 500 let a forecast decide how much Bitcoin he bought. That's not hypocrisy; it's human nature. The more time you pour into a market and the stronger your views about it, the easier it is for those views to overrule your discipline.
Write the "What Ifs" Down First
His answer wasn't a better forecast. It was a script written in advance. Heading into the fourth quarter of 2026, Bitcoin might keep climbing, or it might slip back below the May high. His advice was to plan for both: "If it does this, I'm going to do that. And if it does this, I'm going to do that."
His caution about the fourth quarter of a midterm year has history behind it. In 2014, 2018 and 2022 — all midterm years — Bitcoin sold off late in the year. In 2018 he didn't see it coming; in 2022 he did, for a simple reason: it had happened in the previous two midterm years. But he also learned that even when you call the drop correctly, you can still miss the opportunity if you don't adjust.
He pointed to 2022. That summer Bitcoin drifted between $18,000 and $20,000; in November, FTX collapsed and the price fell further. Two or three years later, it hardly mattered whether someone bought at $18,000 or $15,000. The people who really lost out were the ones too spooked to buy in the summer, even more spooked to buy during the FTX crash, and who then watched the price climb right back. 2018 was the same story: he bought at $6,000 and kept buying as it fell, while others watched it slide, never bought, and only regretted it once it was back at $14,000.
"When you're living through the moment," he said, "it feels really hard."
He also noted that even an FTX-sized drop of about 26% in the fourth quarter would, measured from the high at the time, only take Bitcoin back into the low $60,000s — still above the 2026 low. The next frightening drop isn't necessarily the end of the world. It may just be one more scenario worth preparing for in advance.
That's the real value of a plan: not a promise of the biggest return, but not having to decide on the spot when things are hardest. What reduces stress the most, he has found, is having a plan, sticking to it no matter what, and then getting on with life — because "we only have a small amount of time in this world," and "we don't want to waste it watching a chart."
The Answer Was Already Written Down
Go back to what Cowen said when he first laid out dynamic DCA, and this lesson is already there. He warned that you can't think clearly when the market is ripping higher, or when it's crashing — so set your strategy while things are calm. He was also candid that the approach isn't for everyone: if you know you can't sit and wait, a plain fixed-amount DCA may actually serve you better.
This episode shows how hard both of those are to live by. The framework's own designer — three full market cycles in, someone who has added in low-risk zones and pulled back in high-risk ones — still let "it's going lower" slow his hand during that five-day window in July 2026. If it can happen to him, an ordinary investor has even less reason to believe they'll make their calmest decision at their most emotional moment.
Forecasts Fail. Plans Don't Have to Depend on Them.
Cowen was blunt at the end of his second reflection: if he didn't see Bitcoin breaking the May high, how could he claim to know what comes next? Rather than predicting the short term, he said, build a plan you can carry out whatever happens. When the market goes somewhere he thought it couldn't, he has to humble himself — look for what he's missing and try to understand what the market is actually doing; sometimes even stepping away from the charts for a while is worth it. And he encouraged listening to other views instead of living in an echo chamber.
That may be the most useful thing to take from all of this. Being wrong isn't the danger; anyone who stays in the market long enough will be wrong. The real risk is letting a view decide whether you keep investing. What an analyst who publicly admitted his mistake left behind wasn't a new prediction but a humbler reminder: the market doesn't wait for anyone to be ready. All you can do is decide in advance, then follow through.
Based on public analysis by crypto analyst Benjamin Cowen (Into The Cryptoverse); views expressed are his own. Bitcoin prices reflect public market data as of late September 2026. This article is educational and does not constitute investment advice.