Dylan Jovine made two market calls between 2006 and 2009 that define what he does as an investor. He told his readers to get defensive in December 2006 — 10 months before the market peaked and 21 months before the crash. He told them to go all-in in early 2009 — right at the bottom.

Both were right. The second one made the first one matter.

The Warning

On June 9, 2006, Jovine published a post on his personal blog called “Inside the Markets Recent Drop.” The market had just pulled back about 1,000 points from its highs. The front page of Barron’s that week quoted fund managers predicting the Dow would hit 12,000. Everyone was bullish.

Jovine was not.

“I predicted the market was going to drop,” he wrote. He was explicit that the call was structural analysis, not a brag. His reason was structural: the market was at the peak of a cyclical economic expansion and had “no place else to go but down.”

He published a direct excerpt from his April 2006 issue of Fallen Angel Stocks titled “Why the Stock Market is Overvalued.” The argument was straightforward. The economy looked fine because it was at the top of a cycle. Interest rates were rising. Gas prices were climbing. Consumer spending — two-thirds of the economy — was about to slow.

“Sure, it may trade higher or lower by a few hundred points here and there,” he wrote, “but there is not one good reason why the market should trade higher. All the good news is already priced in.”

The key line: “Yes, I think the market as a whole has no place else to go but down. It is not a question of ‘if.’ It is a question of ‘when.’”

He was writing this in April 2006. The Dow was around 11,000. It would go to 14,000 before it crashed.

On December 19, 2006 — after more than six months of continued bearish writing — he made the warning official. This is the date that appears on every biography page for Jovine as “the first of several public warnings about the stock market to his readers.”

The market peaked in October 2007 at Dow 14,164. By March 2009, it was at 6,547. A 54% decline from peak to trough.

Jovine was not the only person to call the crash. But he was early enough that many of his readers sat out the final 3,000-point run from 11,000 to 14,000 while the bulls laughed. Being early is painful. The market can stay irrational longer than you can stay solvent, as the saying goes. Jovine was early by about 16 months on the formal warning date, and roughly 16 months on the initial April 2006 analysis.

The pain of being early was worth it.

The Bottom Call

When the market was at its darkest point in early 2009, Jovine flipped. He told his readers this would be “the greatest opportunity since the Great Depression.”

He was so convinced that he went on Fox Business to make the case on national television. He was terrible on camera — he admits this himself. “I was never invited back because I was terrible in front of the news camera,” his bio says. The man who could write a clear, compelling market thesis on paper could not deliver it in a three-minute TV segment.

The substance of what he said was right. The market bottomed in March 2009 and went on to produce the longest bull run in American history.

The S&P 500 returned roughly 400% from the March 2009 low to the February 2020 peak. An investor who followed Jovine’s advice — defensive through 2007-2008, then aggressively positioned from early 2009 — would have outperformed almost any strategy.

The AOL Contest

In between the warning and the bottom call, Jovine entered the only investing contest of his career. In 2007, AOL sponsored a competition featuring 100 of the most popular investors in America. Jovine came in second place.

The details of his stock picks in that contest are thin — no one kept good records of a 2007 online contest. Finishing second out of 100 well-known investors during a year when the market was making its final run to the top is the part that matters. He was bearish publicly but still managed to compete with the bulls in a contest format. That tells you something about stock selection versus market timing — he could do both.

What the Story Says

The 2006-2009 period is the most important three years in Jovine’s track record for two reasons.

First, it shows he can think independently. Every bull on Wall Street was screaming that the Goldilocks economy would last forever. Jovine looked at the same data — rising rates, peak cycle economics, consumer strain — and reached the opposite conclusion. He was right.

Second, it shows he learned the right lesson from being early. A lot of bears who called the top at Dow 11,000 stayed bearish all the way to Dow 6,500 and beyond. They were right about the direction but wrong about the timing in a way that cost their followers money. Jovine’s 2009 flip — from defensive to aggressive — shows he understood that markets are cycles, not permanent states. The same instinct that told him the top was in told him the bottom was in. He listened both times.

The 2009 Fox Business appearance is the human detail that makes the story work. A former Wall Street broker who had sold a company to Agora and served 500,000 readers goes on national TV, delivers the call of a lifetime, and is so bad at it that he never gets invited back. The call was right. The delivery was a disaster. That kind of self-awareness — putting the failure on his own bio page — is rare in the newsletter business. Most people would let that story die. Jovine tells it himself.

The Pattern

Jovine’s 2006 warning and 2009 call are not a one-off. They fit a pattern of early-cycle thinking that shows up throughout his career. In 2020, during the COVID crash, he published “4 Steps to Profit from this Market Panic” on March 12 — the exact week of the bottom. He told readers to write a shopping list of stocks they had always wanted to own but missed. He mentioned Starbucks specifically — a stock he had bought at $13.75 during the 2008-2009 crash that later traded at $100.

He was right in 2006, right in 2009, and right again during the COVID crash in 2020 — three market dislocations where his timing was within weeks of the turn. The pattern is not luck. It is a framework for reading cycles and acting on the evidence.

The question every investor should ask: does he still have that instinct in 2026?