The promo pages show Facebook at $100 billion, Apple at $1 trillion, Bitcoin at $114. They skip the $15 million he lost in two years, the hedge fund he shut down because he could not tell which of his investments were fraudulent, and the 17 companies that went nowhere. The wins are real. The failures are documented the same way, in the same archives, by Altucher himself. Both halves matter.
Fifteen million to $143
In August 1998, Altucher sold Reset Inc., the web design firm he co-founded, in a merger with X-ceed Inc. The SEC 8-K filing dated August 5, 1998, lists the principal shareholders as James Altucher, Michel Maitenaz, and Adrian Oradean. Reset’s clients included HBO, the Wall Street Journal, Time Warner, and Con Edison. The websites for the movies “Scream” and “The Matrix” were Reset projects. The deal valued the company at approximately $15 million. The Altucher dossier covers the arc from this exit through the wreckage that followed.
Two years later, the money was gone. Altucher has written about this on his blog, in a post titled “How I Lost $15 Million,” and on CNBC in August 2017. He invested the proceeds into internet stocks at the top of the dot-com bubble, doubling down as they fell and then tripling down. He mortgaged his apartment and borrowed against his house. His wife asked whether he was sure, calling it their last money, and he continued buying.
The end result was $143 in an ATM account. Fifteen million to $143, a collapse he has described in detail across multiple platforms with specific dates and dollar amounts. The sequence is the mirror image of the Facebook call: same pattern recognition, same conviction, opposite outcome. The skill that identified a technology adoption curve before the market priced it in also produced concentrated bets that wiped him out when the curve bent the wrong way.
Jim Cramer hired him to write about stocks for TheStreet.com during this period. The writing gig was how Altucher transitioned from entrepreneur to market commentator, and eventually to the hedge fund career that came next.
The fund of twelve failures
Around 2004, Altucher started a fund of hedge funds. The structure is straightforward: investors give you money, you allocate it across multiple hedge funds, and you take a cut for selecting the right managers. The pitch is access and diversification. The problem was that Altucher could not tell which funds were legitimate and which were frauds.
In a CNBC interview from August 2017, he said that in retrospect, 9 or 10 of the 12 funds he was invested in were fraudulent. One fund manager stole $10 million from his fund, the SEC caught him, and the fine was $50,000 before the manager disappeared. On his blog, in a post titled “I Surrender,” Altucher described the rest: money misallocated to Switzerland and never recovered, at least two Ponzi schemes, kickbacks, lawsuits, and suicides that looked like murders.
The fund’s main investor had put in roughly $20 million. Four months in, the investor demanded his money back, claiming he had never told his own investors he was allocating to a fund of funds and had promised them liquidity. Altucher could not return the money for a year because it was locked in the underlying funds. He spent months clawing it back, piece by piece, $3 million here, $2 million there, until the investor was paid.
Then he shut the fund down. His investors were angry, but the irony, which Altucher has acknowledged, is that shutting down saved them from the 2008 housing crisis. Had they stayed in a few months longer, they would have gotten 40 cents on the dollar; instead, they all made money.
He started another hedge fund at age 39 that lasted two months before he shut it down as well.
The fund of hedge funds episode is the failure that shaped his investing philosophy most directly. He has said that the experience taught him that Wall Street is rigged against the individual investor, that capitalism works but the financial intermediation layer is rotten, and that the only reliable edge is building things yourself. That is the origin of the Choose Yourself philosophy. The book came out of the wreckage.
Seventeen dead companies
Altucher has started roughly 20 companies. By his own count, 17 of them failed. He documented the tally in a blog post titled “16 Failures out of 17 Attempts,” later updated to 17 out of 20 as he started more ventures.
The failures include a crowdsourced advertising venture with the Freakonomics authors, a dating service for Twitter users called 140love, a site called smartorstupid.com that his six-year-old daughter told him was too mean, and a beauty products site called keauty.com that he followed with celebritykeauty.com. Some of the ideas were, by his own admission, the kind that belong in a mental institution.
The individual failed companies do not matter as much as the distribution they form. Altucher swings often, connects on a few, and misses on most. The Buddy Media investment, the StockPickr sale to TheStreet.com for $10 million, and the Reset Inc. merger are the hits, and the 17 others are the misses. The hit rate is low, but the magnitude of the hits, when they land, is what carries the record.
This is the same structure as his market calls. Facebook, Apple, and Bitcoin were massive. The calls that went sideways, the predictions that arrived late or not at all, and the stocks that went nowhere are the rest of the distribution. The framework produces a wide spread of outcomes, and the tails are what matter.
Two lost houses
Altucher bought a multi-million dollar mansion with cryptocurrency earnings. He has described it on his blog and in promotional material as “the house that crypto built.” The purchase was funded by the Bitcoin gains that followed his 2013 call, when the coin was trading at $114.
He lost the house when the crypto market turned. On his blog, in a post about homeownership, he wrote that he has owned two homes and lost both. The first was lost during the dot-com wipeout. The second was lost when crypto pulled back. The pattern is the same one that produced the $15 million to $143 collapse: concentrated bets in volatile assets, held with conviction, unwound by the market.
The mansion story is worth noting because it sits at the intersection of his biggest win and his biggest weakness. The Bitcoin call was correct. The gains were real. The decision to pour those gains into a single illiquid asset exposed him to the same downside he had already experienced with internet stocks a decade earlier. The skill and the flaw are the same trait.
What the failures tell you
Altucher’s blog, going back to 2010, carries both halves of the record — the wins and the failures — in his own writing, in his books, and in interviews with CNBC, TechCrunch, and the Financial Times. The track record articles on this site cover the calls that worked, and this one covers the ones that did not. The full distribution is the record.
The failures share a structure with the wins. Altucher identifies a trend, commits capital with conviction, and either the trend arrives on his timeline or it does not. When it arrives, the magnitude is large. When it does not, the loss is total. The Facebook call and the $15 million wipeout are the same trade in opposite directions. The Bitcoin store and the lost mansion are the same position held too long.
The honesty about the failures is the part that separates Altucher from most newsletter publishers. He has written about being broke, about losing his marriage, about sleeping on friends’ couches, and about starting over with nothing. That willingness to document the full distribution — wins and failures alike — is what makes the track record usable, because you know the shape of the outcome range before you read a single current recommendation.
The framework produces a wide spread of outcomes, and the magnitude of the winners is what carries the average across a full cycle. The frequency of the losers is what tests your patience. Both are part of the same method, and both are documented the same way. The track record of the big calls sits on the other side of this distribution — the hits this piece is the complement to.